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Query
Query
Results
Date
1. Query
O
O
4 citations
2011-06-13 13h:14m:44s (EST)
Search as: Product, As drawn, No salts, No mixtures
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Giri, Ramesh; Maugel, Nathan; Li, Jiao-Jie; Wang, Dong-Hui; Breazzano, Steven P.; Saunders, Lindsey B.; Yu, Jin-Quan
Palladium-Catalyzed Methylation and Arylation of sp
2
and sp
3
C-H Bonds in Simple Carboxylic Acids
Journal of the American Chemical Society; vol. 129; nb. 12; (2007); p. 3510 - 3511
reaction 1 of 45 / citation 1 of 4
HO
O
Cl
O
HO
HO
O
O
O
Yield
Conditions & References
reaction 2 of 45 / citation 1 of 4
OH
O
O
O
O
Yield
Conditions & References
49 mg
With oxalyl dichloride in dichloromethane, T= 0 - 20 °C
reaction 3 of 45 / citation 1 of 4
HO
O
I
OH
O
Yield
Conditions & References
95 %
With dipotassium hydrogenphosphate, sodium acetate, silver carbonate, palladium diacetate in tert-butyl alcohol,
Time= 3h, T= 130 °C
reaction 4 of 45 / citation 1 of 4
HO
O
B
(v3)
OH
HO
HO
O
Yield
Conditions & References
75 %
With dipotassium hydrogenphosphate, silver carbonate, p-benozquinone, palladium diacetate in tert-butyl alcohol,
Time= 3h, T= 100 °C
reaction 5 of 45 / citation 1 of 4
HO
O
O
O
B
(v3)
OH
O
Yield
Conditions & References
63 %
With dipotassium hydrogenphosphate, silver carbonate, p-benozquinone, palladium diacetate in tert-butyl alcohol,
Time= 3h, T= 120 °C
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reaction 6 of 45 / citation 1 of 4
OH
O
HO
O
O
Yield
Conditions & References
28 %
Stage 1: With oxalyl dichloride in dichloromethane, T= 0 - 20 °C
Stage 2: With triethylamine in dichloromethane, Time= 8h, T= 0 - 20 °C , Further stages.
reaction 7 of 45 / citation 1 of 4
HO
I
HO
O
O
O
O
O
Yield
Conditions & References
58 %, 14 %
Stage 1: With dipotassium hydrogenphosphate, sodium acetate, silver carbonate, palladium diacetate in tert-butyl
alcohol, Time= 3h, T= 120 °C
Stage 2: With oxalyl dichloride in dichloromethane, T= 0 - 20 °C
Stage 3: With triethylamine in dichloromethane, Time= 8h, T= 0 - 20 °C , Further stages.
reaction 8 of 45 / citation 1 of 4
HO
I
HO
O
O
O
O
O
Yield
Conditions & References
50 %, 12 %
Stage 1: With dipotassium hydrogenphosphate, sodium acetate, silver carbonate, palladium diacetate in tert-butyl
alcohol, Time= 3h, T= 120 °C
Stage 2: With oxalyl dichloride in dichloromethane, T= 0 - 20 °C
Stage 3: With triethylamine in dichloromethane, Time= 8h, T= 0 - 20 °C , Further stages.
reaction 9 of 45 / citation 1 of 4
HO
I
HO
O
O
O
O
O
O
O
Yield
Conditions & References
42 %
Stage 1: With dipotassium hydrogenphosphate, silver carbonate, p-benozquinone, palladium diacetate in tert-butyl
alcohol, Time= 3h, T= 120 °C
Stage 2: With oxalyl dichloride in dichloromethane, T= 0 - 20 °C
Stage 3: With triethylamine in dichloromethane, Time= 8h, T= 0 - 20 °C , Further stages.
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reaction 10 of 45 / citation 1 of 4
HO
HO
O
I
O
O
O
O
Yield
Conditions & References
45 %, 15 %
Stage 1: With dipotassium hydrogenphosphate, sodium acetate, silver carbonate, palladium diacetate in tert-butyl
alcohol, Time= 3h, T= 120 °C
Stage 2: With oxalyl dichloride in dichloromethane, T= 0 - 20 °C
Stage 3: With triethylamine in dichloromethane, Time= 8h, T= 0 - 20 °C , Further stages.
reaction 11 of 45 / citation 1 of 4
HO
HO
O
I
Br
O
O
Br
O
O
Br
Br
Yield
Conditions & References
47 %, 16 %
Stage 1: With dipotassium hydrogenphosphate, sodium acetate, silver carbonate, palladium diacetate in tert-butyl
alcohol, Time= 3h, T= 120 °C
Stage 2: With oxalyl dichloride in dichloromethane, T= 0 - 20 °C
Stage 3: With triethylamine in dichloromethane, Time= 8h, T= 0 - 20 °C , Further stages.
reaction 12 of 45 / citation 1 of 4
HO
I
HO
O
O
O
O
O
O
O
O
O
O
O
Yield
Conditions & References
36 %, 7 %
Stage 1: With dipotassium hydrogenphosphate, silver carbonate, p-benozquinone, palladium diacetate in tert-butyl
alcohol, Time= 3h, T= 120 °C
Stage 2: With oxalyl dichloride in dichloromethane, T= 0 - 20 °C
Stage 3: With triethylamine in dichloromethane, Time= 8h, T= 0 - 20 °C , Further stages.
reaction 13 of 45 / citation 1 of 4
HO
HO
O
O
O
Yield
Conditions & References
38 %
Stage 1: With oxalyl dichloride in dichloromethane, T= 0 - 20 °C
Stage 2: With triethylamine in dichloromethane, Time= 8h, T= 0 - 20 °C , Further stages.
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5/43
2011-06-13 13:28:23
reaction 14 of 45 / citation 1 of 4
HO
HO
O
O
O
Yield
Conditions & References
30 %
Stage 1: With oxalyl dichloride in dichloromethane, T= 0 - 20 °C
Stage 2: With triethylamine in dichloromethane, Time= 8h, T= 0 - 20 °C , Further stages.
reaction 15 of 45 / citation 1 of 4
HO
HO
O
O
O
B
(v3)
O O
racemate
Yield
Conditions & References
20 %
Stage 1: With dipotassium hydrogenphosphate, silver carbonate, p-benozquinone, palladium diacetate in tert-butyl
alcohol, Time= 3h, T= 120 °C
Stage 2: With oxalyl dichloride in dichloromethane, T= 0 - 20 °C
Stage 3: With triethylamine in dichloromethane, Time= 8h, T= 0 - 20 °C , Further stages.
reaction 16 of 45 / citation 1 of 4
HO
HO
O
O
O
O
O
B
(v3)
O
O
O
O
Yield
Conditions & References
30 %
Stage 1: With dipotassium hydrogenphosphate, silver carbonate, p-benozquinone, palladium diacetate in tert-butyl
alcohol, Time= 3h, T= 120 °C
Stage 2: With oxalyl dichloride in dichloromethane, T= 0 - 20 °C
Stage 3: With triethylamine in dichloromethane, Time= 8h, T= 0 - 20 °C , Further stages.
reaction 17 of 45 / citation 1 of 4
HO
O
O
B
(v3)
O
O
–
Na
+
(v0)
O
O
Yield
Conditions & References
30 %
Stage 1: With silver carbonate, p-benozquinone, palladium diacetate in tert-butyl alcohol, Time= 3h, T= 120 °C
Stage 2: With oxalyl dichloride in dichloromethane, T= 0 - 20 °C
Stage 3: With triethylamine in dichloromethane, Time= 8h, T= 0 - 20 °C , Further stages.
reaction 18 of 45 / citation 1 of 4
OH
O
O
I
O
O
O
O
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Yield
Conditions & References
37 %, 8 %
Stage 1: With dipotassium hydrogenphosphate, sodium acetate, silver carbonate, palladium diacetate in tert-butyl
alcohol, Time= 3h, T= 120 °C
Stage 2: With oxalyl dichloride in dichloromethane, T= 0 - 20 °C , Further stages.
reaction 19 of 45 / citation 1 of 4
I
O
O
–
Na
+
(v0)
O
–
O
Na
+
(v0)
O
–
O
Na
+
(v0)
Yield
Conditions & References
With silver carbonate, palladium diacetate in tert-butyl alcohol, Time= 3h, T= 130 °C , Product distribution, Further
Variations: Solvents
reaction 20 of 45 / citation 1 of 4
HO
O
O
O
B
(v3)
HO
O
Yield
Conditions & References
With dipotassium hydrogenphosphate, silver carbonate, p-benozquinone, palladium diacetate in tert-butyl alcohol,
Time= 3h, T= 120 °C
reaction 21 of 45 / citation 1 of 4
B
(v3)
OH
HO
O
O
–
K
+
(v0)
HO
O
Yield
Conditions & References
48 %
With silver carbonate, p-benozquinone, palladium diacetate in tert-butyl alcohol, Time= 3h, T= 100 °C
reaction 22 of 45 / citation 1 of 4
B
(v3)
OH
HO
O
O
–
Na
+
(v0)
HO
O
Yield
Conditions & References
50 %
With silver carbonate, p-benozquinone, palladium diacetate in tert-butyl alcohol, Time= 3h, T= 100 °C
reaction 23 of 45 / citation 1 of 4
O
O
O
Br
OH
O
O
Yield
Conditions & References
Stage 1:
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2011-06-13 13:28:23
Stage 2: With water, Alkaline hydrolysis, Further stages.
reaction 24 of 45 / citation 1 of 4
HO
O
O
O
B
(v3)
OH
O
Yield
Conditions & References
With dipotassium hydrogenphosphate, silver carbonate, p-benozquinone, palladium diacetate in tert-butyl alcohol,
Time= 3h, T= 120 °C
reaction 25 of 45 / citation 1 of 4
O
O
OH
O
O
O
B
(v3)
HO
O
O
O
Yield
Conditions & References
40 %
With dipotassium hydrogenphosphate, silver carbonate, p-benozquinone, palladium diacetate in tert-butyl alcohol,
Time= 3h, T= 120 °C
reaction 26 of 45 / citation 1 of 4
HO
O
O
O
O
O
B
(v3)
OH
O
O
O
Yield
Conditions & References
With dipotassium hydrogenphosphate, silver carbonate, p-benozquinone, palladium diacetate in tert-butyl alcohol,
Time= 3h, T= 120 °C
reaction 27 of 45 / citation 1 of 4
OH
O
O
O
O
B
(v3)
OH
O
O
Yield
Conditions & References
With dipotassium hydrogenphosphate, silver carbonate, p-benozquinone, palladium diacetate in tert-butyl alcohol,
Time= 3h, T= 120 °C
reaction 28 of 45 / citation 1 of 4
O
O
B
(v3)
O
O
–
Na
+
(v0)
OH
O
Yield
Conditions & References
45 %
With silver carbonate, p-benozquinone, palladium diacetate in tert-butyl alcohol, Time= 3h, T= 120 °C
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reaction 29 of 45 / citation 1 of 4
B
(v3)
OH
HO
HO
O
O
OH
O
O
Yield
Conditions & References
71 %
With dipotassium hydrogenphosphate, silver carbonate, p-benozquinone, palladium diacetate in tert-butyl alcohol,
Time= 3h, T= 100 °C
reaction 30 of 45 / citation 1 of 4
O
O
B
(v3)
HO
O
O
OH
O
O
Yield
Conditions & References
46 %
With dipotassium hydrogenphosphate, silver carbonate, p-benozquinone, palladium diacetate in tert-butyl alcohol,
Time= 3h, T= 120 °C
reaction 31 of 45 / citation 1 of 4
HO
I
HO
O
O
O
O
O
Yield
Conditions & References
50 %, 20 %
Stage 1: With dipotassium hydrogenphosphate, sodium acetate, silver carbonate, palladium diacetate in tert-butyl
alcohol, Time= 3h, T= 120 °C
Stage 2: With oxalyl dichloride in dichloromethane, T= 0 - 20 °C
Stage 3: With triethylamine in dichloromethane, Time= 8h, T= 0 - 20 °C , Further stages.
reaction 32 of 45 / citation 1 of 4
O
O
B
(v3)
HO
O
HO
O
Yield
Conditions & References
With dipotassium hydrogenphosphate, silver carbonate, p-benozquinone, palladium diacetate in tert-butyl alcohol,
Time= 3h, T= 120 °C
reaction 33 of 45 / citation 1 of 4
O
O
B
(v3)
HO
O
OH
O
Yield
Conditions & References
50 %
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With dipotassium hydrogenphosphate, silver carbonate, p-benozquinone, palladium diacetate in tert-butyl alcohol,
Time= 3h, T= 120 °C
reaction 34 of 45 / citation 1 of 4
HO
O
Cl
O
O
O
O
O
Yield
Conditions & References
Reaction Steps: 2
1.1: Ag
2
CO
3
; K
2
HPO
4
; benzoquinone / Pd(OAc)2 / 2-methyl-propan-2-ol / 3 h / 120 °C
1.2: oxalyl chloride / CH
2
Cl
2
/ 0 - 20 °C
1.3: 42 percent / triethylamine / CH
2
Cl
2
/ 8 h / 0 - 20 °C
With dipotassium hydrogenphosphate, silver carbonate, p-benozquinone, palladium diacetate in tert-butyl alcohol
reaction 35 of 45 / citation 1 of 4
HO
O
Cl
O
OH
O
O
O
Yield
Conditions & References
Reaction Steps: 2
1: Ag
2
CO
3
; K
2
HPO
4
; benzoquinone / Pd(OAc)2 / 2-methyl-propan-2-ol / 3 h / 120 °C
With dipotassium hydrogenphosphate, silver carbonate, p-benozquinone, palladium diacetate in tert-butyl alcohol
reaction 36 of 45 / citation 1 of 4
HO
O
Cl
O
O
O
O
O
Yield
Conditions & References
Reaction Steps: 2
1.1: Ag
2
CO
3
; K
2
HPO
4
; benzoquinone / Pd(OAc)2 / 2-methyl-propan-2-ol / 3 h / 120 °C
1.2: oxalyl chloride / CH
2
Cl
2
/ 0 - 20 °C
1.3: 36 percent / triethylamine / CH
2
Cl
2
/ 8 h / 0 - 20 °C
With dipotassium hydrogenphosphate, silver carbonate, p-benozquinone, palladium diacetate in tert-butyl alcohol
reaction 37 of 45 / citation 1 of 4
HO
O
Cl
O
O
O
O
O
Yield
Conditions & References
Reaction Steps: 2
1.1: Ag
2
CO
3
; K
2
HPO
4
; benzoquinone / Pd(OAc)2 / 2-methyl-propan-2-ol / 3 h / 120 °C
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1.2: oxalyl chloride / CH
2
Cl
2
/ 0 - 20 °C
1.3: 7 percent / triethylamine / CH
2
Cl
2
/ 8 h / 0 - 20 °C
With dipotassium hydrogenphosphate, silver carbonate, p-benozquinone, palladium diacetate in tert-butyl alcohol
reaction 38 of 45 / citation 1 of 4
OH
O
O
O
O
Yield
Conditions & References
Reaction Steps: 2
1: benzoquinone; Ag
2
CO
3
; K
2
HPO
4
/ Pd(OAc)2 / 2-methyl-propan-2-ol / 3 h / 120 °C
2: 49 mg / oxalyl chloride / CH
2
Cl
2
/ 0 - 20 °C
With dipotassium hydrogenphosphate, oxalyl dichloride, silver carbonate, p-benozquinone, palladium diacetate in di-
chloromethane, tert-butyl alcohol
reaction 39 of 45 / citation 1 of 4
HO
O
O
O
Yield
Conditions & References
Reaction Steps: 2
1.1: Ag
2
CO
3
; K
2
HPO
4
; benzoquinone / Pd(OAc)2 / 2-methyl-propan-2-ol / 3 h / 120 °C
2.1: oxalyl chloride / CH
2
Cl
2
/ 0 - 20 °C
2.2: 30 percent / triethylamine / CH
2
Cl
2
/ 8 h / 0 - 20 °C
With dipotassium hydrogenphosphate, oxalyl dichloride, silver carbonate, p-benozquinone, palladium diacetate in di-
chloromethane, tert-butyl alcohol
reaction 40 of 45 / citation 1 of 4
HO
O
O
O
Yield
Conditions & References
Reaction Steps: 2
1.1: Ag
2
CO
3
; K
2
HPO
4
; benzoquinone / Pd(OAc)2 / 2-methyl-propan-2-ol / 3 h / 120 °C
2.1: oxalyl chloride / CH
2
Cl
2
/ 0 - 20 °C
2.2: 28 percent / triethylamine / CH
2
Cl
2
/ 8 h / 0 - 20 °C
With dipotassium hydrogenphosphate, oxalyl dichloride, silver carbonate, p-benozquinone, palladium diacetate in di-
chloromethane, tert-butyl alcohol
reaction 41 of 45 / citation 1 of 4
O
Br
OH
O
O
Yield
Conditions & References
Reaction Steps: 2
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1.2: H
2
O / Alkaline hydrolysis
2.1: benzoquinone; Ag
2
CO
3
; K
2
HPO
4
/ Pd(OAc)2 / 2-methyl-propan-2-ol / 3 h / 120 °C
With dipotassium hydrogenphosphate, silver carbonate, p-benozquinone, palladium diacetate in tert-butyl alcohol
reaction 42 of 45 / citation 1 of 4
O
Br
O
O
Yield
Conditions & References
Reaction Steps: 2
1.2: H
2
O / Alkaline hydrolysis
2.1: Ag
2
CO
3
; K
2
HPO
4
; sodium acetate / Pd(OAc)2 / 2-methyl-propan-2-ol / 3 h / 120 °C
2.2: 8 percent / oxalyl chloride / CH
2
Cl
2
/ 0 - 20 °C
With dipotassium hydrogenphosphate, sodium acetate, silver carbonate, palladium diacetate in tert-butyl alcohol
reaction 43 of 45 / citation 1 of 4
O
O
B
(v3)
O
O
Yield
Conditions & References
Reaction Steps: 2
1.1: Ag
2
CO
3
; K
2
HPO
4
; benzoquinone / Pd(OAc)2 / 2-methyl-propan-2-ol / 3 h / 120 °C
2.1: oxalyl chloride / CH
2
Cl
2
/ 0 - 20 °C
2.2: 28 percent / triethylamine / CH
2
Cl
2
/ 8 h / 0 - 20 °C
With dipotassium hydrogenphosphate, oxalyl dichloride, silver carbonate, p-benozquinone, palladium diacetate in di-
chloromethane, tert-butyl alcohol
reaction 44 of 45 / citation 1 of 4
O
O
B
(v3)
O
O
Yield
Conditions & References
Reaction Steps: 2
1.1: Ag
2
CO
3
; K
2
HPO
4
; benzoquinone / Pd(OAc)2 / 2-methyl-propan-2-ol / 3 h / 120 °C
2.1: oxalyl chloride / CH
2
Cl
2
/ 0 - 20 °C
2.2: 38 percent / triethylamine / CH
2
Cl
2
/ 8 h / 0 - 20 °C
With dipotassium hydrogenphosphate, oxalyl dichloride, silver carbonate, p-benozquinone, palladium diacetate in di-
chloromethane, tert-butyl alcohol
reaction 45 of 45 / citation 1 of 4
O
O
B
(v3)
O
O
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Yield
Conditions & References
Reaction Steps: 2
1.1: Ag
2
CO
3
; K
2
HPO
4
; benzoquinone / Pd(OAc)2 / 2-methyl-propan-2-ol / 3 h / 120 °C
2.1: oxalyl chloride / CH
2
Cl
2
/ 0 - 20 °C
2.2: 30 percent / triethylamine / CH
2
Cl
2
/ 8 h / 0 - 20 °C
With dipotassium hydrogenphosphate, oxalyl dichloride, silver carbonate, p-benozquinone, palladium diacetate in di-
chloromethane, tert-butyl alcohol
O
O
XRN = 216771
HO
O
O
XRN = 508838
Identification (4)
Physical Data (1)
Spectra (6)
Identification (94)
Physical Data (151)
Spectra (66)
Bioactivity/Ecotox (25)
Use/Application (8)
Natural Product (1)
HO
O
XRN = 969480
HO
O
XRN = 970526
Identification (161)
Physical Data (330)
Spectra (91)
Bioactivity/Ecotox (16)
Use/Application (31)
Identification (109)
Physical Data (353)
Spectra (70)
Bioactivity/Ecotox (12)
Use/Application (2)
Natural Product (2)
HO
O
XRN = 1072103
HO
XRN = 1098229
Identification (144)
Physical Data (459)
Spectra (84)
Bioactivity/Ecotox (12)
Use/Application (4)
Natural Product (1)
Identification (744)
Physical Data (6932)
Spectra (523)
Bioactivity/Ecotox (445)
Use/Application (453)
Natural Product (6)
I
XRN = 1446140
HO
O
XRN = 1720666
Identification (132)
Physical Data (658)
Spectra (173)
Bioactivity/Ecotox (9)
Use/Application (2)
Identification (42)
Physical Data (69)
Spectra (15)
Bioactivity/Ecotox (7)
B
(v3)
OH
HO
XRN = 1731087
O
O
XRN = 1740720
Identification (43)
Physical Data (35)
Spectra (12)
Use/Application (6)
Identification (59)
Physical Data (148)
Spectra (64)
Bioactivity/Ecotox (5)
Natural Product (1)
HO
O
XRN = 1747703
HO
O
XRN = 1749961
Identification (26)
Physical Data (34)
Spectra (9)
Identification (20)
Physical Data (22)
Spectra (10)
HO
O
XRN = 1863791
I
XRN = 1903637
Identification (42)
Physical Data (101)
Spectra (26)
Bioactivity/Ecotox (4)
Identification (302)
Physical Data (149)
Spectra (82)
Bioactivity/Ecotox (4)
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I
Br
XRN = 1904545
HO
O
XRN = 1943807
Identification (151)
Physical Data (71)
Spectra (45)
Identification (22)
Physical Data (13)
Spectra (8)
HO
O
XRN = 1950675
HO
O
XRN = 2039384
Identification (5)
Physical Data (3)
Identification (21)
Physical Data (19)
Spectra (7)
O
O
OH
O
XRN = 2048750
O
Br
XRN = 2084412
Identification (31)
Physical Data (28)
Spectra (18)
Identification (19)
Physical Data (9)
Spectra (17)
O
O
XRN = 2209134
O
O
XRN = 2210249
Identification (15)
Physical Data (12)
Spectra (15)
Identification (5)
Physical Data (1)
Spectra (6)
HO
O
O
O
XRN = 2438976
OH
O
XRN = 2615708
Identification (5)
Physical Data (1)
Spectra (1)
Identification (8)
Physical Data (4)
Spectra (18)
OH
O
XRN = 2615735
OH
O
O
XRN = 2691041
Identification (4)
Physical Data (6)
Spectra (11)
Identification (11)
Physical Data (14)
Spectra (15)
OH
O
O
XRN = 2695471
O
O
B
(v3)
XRN = 2936745
Identification (7)
Physical Data (2)
Spectra (10)
Identification (27)
Physical Data (10)
Spectra (19)
O
O
–
K
+
(v0)
XRN = 3727012
O
O
XRN = 3946519
Identification (6)
Physical Data (1)
Identification (5)
Physical Data (1)
Spectra (7)
O
O
–
Na
+
(v0)
XRN = 4027569
O
O
–
Na
+
(v0)
XRN = 4158485
Identification (11)
Physical Data (5)
Spectra (4)
Identification (17)
Physical Data (1)
Spectra (5)
Bioactivity/Ecotox (14)
Use/Application (1)
O O
racemate
XRN = 4673695
HO
O
Cl
O
XRN = 10425020
Identification (8)
Spectra (10)
Identification (3)
OH
O
XRN = 10663113
O
O
XRN = 10663822
Identification (4)
Identification (4)
Spectra (6)
Copyright © 2011 Elsevier Properties SA. All rights reserved. Authorized use only.
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under license.
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2011-06-13 13:28:23
O
O
XRN = 10663919
O
O
XRN = 10666256
Identification (4)
Spectra (6)
Identification (4)
Spectra (6)
O
O
O
O
XRN = 10666762
O
O
Br
XRN = 10666834
Identification (4)
Spectra (6)
Identification (4)
Spectra (6)
OH
O
O
XRN = 10667209
OH
O
O
O
XRN = 10669724
Identification (4)
Identification (4)
HO
O
O
O
XRN = 10669800
O
O
XRN = 10670975
Identification (4)
Spectra (6)
Identification (4)
Spectra (6)
O
O
O
O
XRN = 10672965
O
O
XRN = 10681819
Identification (4)
Spectra (6)
Identification (4)
Spectra (6)
OH
O
O
XRN = 10686147
O
O
XRN = 10689385
Identification (4)
Identification (4)
Spectra (6)
O
O
Br
Br
XRN = 10693131
O
O
O
O
XRN = 10701479
Identification (4)
Spectra (6)
Identification (4)
Spectra (6)
O
–
O
Na
+
(v0)
XRN = 10721220
O
–
O
Na
+
(v0)
XRN = 10732899
Identification (3)
Identification (3)
Copyright © 2011 Elsevier Properties SA. All rights reserved. Authorized use only.
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under license.
15/43
2011-06-13 13:28:23
Hexachimie Societe Anonyme
Indaneacetic acid derivatives
Patent: US4166131; (1979); (A1)
Abstract: This invention provides new compounds of formula I, STR1 wherein R
1
is lower alkyl, R
2
is hydrogen or lower alkyl, R
3
is
hydrogen or lower alkyl, R
4
is hydrogen or lower alkyl, R
5
is hydrogen, chlorine or lower alkyl, and each of R
6
and R
7
is hydrogen,
or, when R
5
is hydrogen, R
6
may also be chlorine or lower alkyl, and R
7
chlorine or lower alkyl, Useful as anti-phlogistic and anti-
arthritic agents.
Patent Assignee / Inventors
Assignees
Inventors (Authors)
Hexachimie Societe Anonyme
Payne; Trevor G.
Publication / Application Data
Patent No
Kind Code
Publ. Date
Application No
Filing Date
Indexed Patent
US4166131
A1
1979/08/28
US1974-517531
1974/10/24
yes
CH1973-15251
1973/10/30
Priority Data
Priority No
Priority Date
CH1973-15251
1973/10/30
Patent Classification
Main IPC
C07C 63/337
Secondary IPC
A61K 31/19; A61K 31/215; C07C 69/76
reaction 1 of 65 / citation 2 of 4
O
Yield
Conditions & References
Example Name 8.d
Example Title 2-methyl-5-indanacetic acid
With hydrogenchloride, palladium charcoal in ethanol
reaction 2 of 65 / citation 2 of 4
O
O
Cl
O
O
Yield
Conditions & References
Example Name 16.a
Example Title 2,2-dimethyl-5-indanacetic acid
reaction 3 of 65 / citation 2 of 4
O
O
Cl
Cl
O
O
Cl
Yield
Conditions & References
Example Name 17.a
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Example Title 6-chloro-2,2-dimethyl-5-indanacetic acid
reaction 4 of 65 / citation 2 of 4
O
Yield
Conditions & References
Example Name 16.c
Example Title 2,2-dimethyl-5-indanacetic acid
reaction 5 of 65 / citation 2 of 4
O
Yield
Conditions & References
Example Name 9.c
Example Title 2-ethyl-5-indanacetic acid
reaction 6 of 65 / citation 2 of 4
HO
O
Yield
Conditions & References
Example Name 16.b
Example Title 2,2-dimethyl-5-indanacetic acid
reaction 7 of 65 / citation 2 of 4
HO
O
E
Yield
Conditions & References
Example Name 9.a
Example Title 2-ethyl-5-indanacetic acid
reaction 8 of 65 / citation 2 of 4
HO
O
Yield
Conditions & References
Example Name 9.b
Example Title 2-ethyl-5-indanacetic acid
reaction 9 of 65 / citation 2 of 4
HO
O
E
Yield
Conditions & References
Example Name 8.a
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2011-06-13 13:28:23
Example Title 2-methyl-5-indanacetic acid
reaction 10 of 65 / citation 2 of 4
O
Yield
Conditions & References
Example Name 8.c
Example Title 2-methyl-5-indanacetic acid
reaction 11 of 65 / citation 2 of 4
Cl
Yield
Conditions & References
Example Name 6.d
Example Title 2-ethyl-6-chloro-5-indanacetic acid
reaction 12 of 65 / citation 2 of 4
O
Cl
Yield
Conditions & References
Example Name 17.c
Example Title 6-chloro-2,2-dimethyl-5-indanacetic acid
reaction 13 of 65 / citation 2 of 4
O
Yield
Conditions & References
Example Name 4.c
Example Title 2-ethyl-2,6-dimethyl-5-indanacetic acid
reaction 14 of 65 / citation 2 of 4
HO
O
Yield
Conditions & References
Example Name 19.b
Example Title 2,2,6-trimethyl-5-indanacetic acid
reaction 15 of 65 / citation 2 of 4
O
Yield
Conditions & References
Example Name 7.c
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2011-06-13 13:28:23
Example Title 2-ethyl-6-methyl-5-indanacetic acid
reaction 16 of 65 / citation 2 of 4
O
Cl
Yield
Conditions & References
Example Name 6.c
Example Title 2-ethyl-6-chloro-5-indanacetic acid
reaction 17 of 65 / citation 2 of 4
HO
O
Cl
Yield
Conditions & References
Example Name 17.b
Example Title 6-chloro-2,2-dimethyl-5-indanacetic acid
reaction 18 of 65 / citation 2 of 4
N
Yield
Conditions & References
Example Name 23.b
Example Title 2-ethyl-5-indanacetic acid [process variant (b)]
reaction 19 of 65 / citation 2 of 4
HO
O
Cl
Yield
Conditions & References
Example Name 18.b
Example Title 2-ethyl-6-chloro-2-methyl-5-indanacetic acid
reaction 20 of 65 / citation 2 of 4
HO O
Yield
Conditions & References
Example Name 7
Example Title 2-ethyl-6-methyl-5-indanacetic acid
reaction 21 of 65 / citation 2 of 4
HO
O
Yield
Conditions & References
Example Name 16
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19/43
2011-06-13 13:28:23
Example Title 2,2-dimethyl-5-indanacetic acid
reaction 22 of 65 / citation 2 of 4
HO
O
Yield
Conditions & References
Example Name 8
Example Title 2-methyl-5-indanacetic acid
reaction 23 of 65 / citation 2 of 4
Cl
HO O
Yield
Conditions & References
Example Name 17
Example Title 6-chloro-2,2-dimethyl-5-indanacetic acid
reaction 24 of 65 / citation 2 of 4
HO
O
Yield
Conditions & References
Example Name 14
Example Title 2-ethyl-2-methyl-5-indanacetic acid
reaction 25 of 65 / citation 2 of 4
HO
O
Yield
Conditions & References
Example Name 9
Example Title 2-ethyl-5-indanacetic acid
reaction 26 of 65 / citation 2 of 4
HO
O
Yield
Conditions & References
Example Name 5
Example Title 2-isopropyl-5-indanacetic acid
reaction 27 of 65 / citation 2 of 4
Cl
HO O
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under license.
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2011-06-13 13:28:23
Yield
Conditions & References
Example Name 18
Example Title 2-ethyl-6-chloro-2-methyl-5-indanacetic acid
reaction 28 of 65 / citation 2 of 4
Cl
HO O
Yield
Conditions & References
Example Name 6
Example Title 2-ethyl-6-chloro-5-indanacetic acid
reaction 29 of 65 / citation 2 of 4
O
O O
Yield
Conditions & References
Example Name 7.e
Example Title 2-ethyl-6-methyl-5-indanacetic acid
reaction 30 of 65 / citation 2 of 4
O
O
O
Yield
Conditions & References
Example Name 8.e
Example Title 2-methyl-5-indanacetic acid
reaction 31 of 65 / citation 2 of 4
Cl
O
O O
Yield
Conditions & References
Example Name 6.e
Example Title 2-ethyl-6-chloro-5-indanacetic acid
reaction 32 of 65 / citation 2 of 4
O
O
O
Yield
Conditions & References
Example Name 9.e
Example Title 2-ethyl-5-indanacetic acid
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under license.
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2011-06-13 13:28:23
reaction 33 of 65 / citation 2 of 4
HO
Yield
Conditions & References
Example Name 1.b
Example Title 2-isopropyl-
α-methyl-5-indanacetic acid [process variant (a)]
reaction 34 of 65 / citation 2 of 4
HO
O
Yield
Conditions & References
Example Name 15
Example Title 2,2-diethyl-5-indanacetic acid
reaction 35 of 65 / citation 2 of 4
HO
O
Yield
Conditions & References
Example Name 15.b
Example Title 2,2-diethyl-5-indanacetic acid
reaction 36 of 65 / citation 2 of 4
P
O
O
O
O
O
O
HO
O
E
Yield
Conditions & References
Example Name 7.a
Example Title 2-ethyl-6-methyl-5-indanacetic acid
in methanol
reaction 37 of 65 / citation 2 of 4
O
O
Br
O
O
Yield
Conditions & References
Example Name 19.a
Example Title 2,2,6-trimethyl-5-indanacetic acid
reaction 38 of 65 / citation 2 of 4
O
O
Br
O
O
Yield
Conditions & References
Example Name 4.a
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under license.
22/43
2011-06-13 13:28:23
Example Title 2-ethyl-2,6-dimethyl-5-indanacetic acid
With Hg
reaction 39 of 65 / citation 2 of 4
OH
O
Br
Br
O
O
O
O
O
O
Yield
Conditions & References
Example Name 1.a
Example Title 2-isopropyl-
α-methyl-5-indanacetic acid [process variant (a)]
With hydrogenchloride in methanol
reaction 40 of 65 / citation 2 of 4
Mg
(v2)
I
O
O
O
I
HO
O
O
Yield
Conditions & References
Example Name 1.d
Example Title 2-isopropyl-
α-methyl-5-indanacetic acid [process variant (a)]
With ammonium chloride, magnesium
reaction 41 of 65 / citation 2 of 4
O
O
–
O
Hg
2+
(v0)
2
Yield
Conditions & References
Example Name 3.d
Example Title 2-ethyl-2,
α-dimethyl-5-indanacetic acid
With hydrogenchloride, zinc in ethanol, water
reaction 42 of 65 / citation 2 of 4
OH
O
Cl
O
O
Yield
Conditions & References
Example Name 15.a
Example Title 2,2-diethyl-5-indanacetic acid
reaction 43 of 65 / citation 2 of 4
O
O
Cl
O
O
Yield
Conditions & References
Example Name 3.a
Example Title 2-ethyl-2,
α-dimethyl-5-indanacetic acid
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under license.
23/43
2011-06-13 13:28:23
With acetic acid in tetrahydrofuran, methanol, Petroleum ether
reaction 44 of 65 / citation 2 of 4
O
S
OH
HO O
Cl
Yield
Conditions & References
Example Name 23.a
Example Title 2-ethyl-5-indanacetic acid [process variant (b)]
With hydrogenchloride, formaldehyd in water
reaction 45 of 65 / citation 2 of 4
HO
O
O
O
S
OH
HO O
O
O
Yield
Conditions & References
Example Name 22
Example Title 2-ethyl-2,
α-dimethyl-5-indanacetic acid methyl ester
With Hg, PtO
2
in methanol
reaction 46 of 65 / citation 2 of 4
Cl
O
O
O
O
S
OH
HO O
Cl
O
O
Yield
Conditions & References
Example Name 21
Example Title 2-ethyl-6-chloro-2-methyl-5-indanacetic acid methyl ester
With PtO
2
, hydrogen in methanol
reaction 47 of 65 / citation 2 of 4
O
O
Cl
Cl
O
O
Cl
Yield
Conditions & References
Example Name 18.a
Example Title 2-ethyl-6-chloro-2-methyl-5-indanacetic acid
reaction 48 of 65 / citation 2 of 4
oxalic acid monomethyl ester chloride
O
O
O
Yield
Conditions & References
Example Name 1.c
Example Title 2-isopropyl-
α-methyl-5-indanacetic acid [process variant (a)]
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24/43
2011-06-13 13:28:23
With aluminium chloride in dichloromethane
reaction 49 of 65 / citation 2 of 4
HO
HO
O
HO
O
Yield
Conditions & References
Example Name 1
Example Title 2-isopropyl-
α-methyl-5-indanacetic acid [process variant (a)]
With perchloric acid, sodium acetate, PtO
2
in acetic acid
reaction 50 of 65 / citation 2 of 4
HO
O
O
HO
HO
O
Yield
Conditions & References
Example Name 1.e
Example Title 2-isopropyl-
α-methyl-5-indanacetic acid [process variant (a)]
With potassium hydroxide in methanol, water
reaction 51 of 65 / citation 2 of 4
HO
O
HO
O
Yield
Conditions & References
Example Name 2
Example Title 2-isopropyl-
α-methyl-5-indanacetic acid
With PtO
2
in ethanol
reaction 52 of 65 / citation 2 of 4
HO
HO
O
HO
O
Yield
Conditions & References
Example Name 3
Example Title 2-ethyl-2,
α-dimethyl-5-indanacetic acid
reaction 53 of 65 / citation 2 of 4
O
O O
HO O
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2011-06-13 13:28:23
Yield
Conditions & References
Example Name 4
Example Title 2-ethyl-2,6-dimethyl-5-indanacetic acid
With potassium hydroxide, hydrazine hydrate in diethylene glycol
reaction 54 of 65 / citation 2 of 4
O
O
O
O
HO
O
Yield
Conditions & References
Example Name 5.b
Example Title 2-isopropyl-5-indanacetic acid
With sodium hydroxide in ethanol, water
reaction 55 of 65 / citation 2 of 4
OH
HO
O
Cl
Cl
O
O O
Cl
HO O
Yield
Conditions & References
Example Name 13
Example Title 2-ethyl-6-chloro-
α-methyl-5-indanacetic acid
reaction 56 of 65 / citation 2 of 4
HO
O
Cl
E
HO
O
Cl
Yield
Conditions & References
Example Name 6.b
Example Title 2-ethyl-6-chloro-5-indanacetic acid
With PtO
2
in ethanol
reaction 57 of 65 / citation 2 of 4
OH
HO
O
O
O O
HO O
Yield
Conditions & References
Example Name 10
Example Title 2-ethyl-6,
α-dimethyl-5-indanacetic acid
reaction 58 of 65 / citation 2 of 4
HO
O
E
HO
O
Yield
Conditions & References
Example Name 7.b
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26/43
2011-06-13 13:28:23
Example Title 2-ethyl-6-methyl-5-indanacetic acid
With sodium in methyl-isobutyl-carbinol, water, toluene
reaction 59 of 65 / citation 2 of 4
HO
HO
O
O
O
O
HO
O
Yield
Conditions & References
Example Name 12
Example Title 2,
α-dimethyl-5-indanacetic acid
reaction 60 of 65 / citation 2 of 4
HO
HO
O
O
O
O
HO
O
Yield
Conditions & References
Example Name 11
Example Title 2-ethyl-
α-methyl-5-indanacetic acid
reaction 61 of 65 / citation 2 of 4
HO
HO
O
HO
O
Yield
Conditions & References
Example Name 20
Example Title 2,2,
α-trimethyl-5-indanacetic acid
in ethanol
reaction 62 of 65 / citation 2 of 4
Cl
O
O
Cl
HO O
Yield
Conditions & References
Example Name 25
Example Title 2-ethyl-6-chloro-2-methyl-5-indanacetic acid [process variant (d)]
With potassium hydroxide in methanol, water
reaction 63 of 65 / citation 2 of 4
O
O
HO
O
Yield
Conditions & References
Example Name 3.b
Example Title 2-ethyl-2,
α-dimethyl-5-indanacetic acid
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under license.
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2011-06-13 13:28:23
With potassium hydroxide in methanol, water
reaction 64 of 65 / citation 2 of 4
HO
O
O
Yield
Conditions & References
Example Name 3.c
Example Title 2-ethyl-2,
α-dimethyl-5-indanacetic acid
With PPA in water
reaction 65 of 65 / citation 2 of 4
N
HO
O
Yield
Conditions & References
Example Name 23
Example Title 2-ethyl-5-indanacetic acid [process variant (b)]
With potassium hydroxide in ethanol, water
O
XRN = 385772
Cl
XRN = 471308
Identification (279)
Physical Data (190)
Spectra (151)
Bioactivity/Ecotox (37)
Use/Application (4)
Natural Product (2)
Identification (120)
Physical Data (435)
Spectra (105)
Bioactivity/Ecotox (36)
Use/Application (5)
Cl
Cl
XRN = 471558
Br
XRN = 507389
Identification (113)
Physical Data (69)
Spectra (23)
Bioactivity/Ecotox (1)
Identification (110)
Physical Data (57)
Spectra (15)
Br
Br
XRN = 637159
O
O
O
O
XRN = 774261
Identification (92)
Physical Data (45)
Spectra (14)
Bioactivity/Ecotox (1)
Use/Application (3)
Identification (232)
Physical Data (219)
Spectra (50)
I
XRN = 969135
OH
O
XRN = 1098634
Identification (303)
Physical Data (709)
Spectra (255)
Bioactivity/Ecotox (60)
Use/Application (32)
Identification (64)
Physical Data (74)
Spectra (17)
Bioactivity/Ecotox (13)
Use/Application (2)
Mg
(v2)
I
XRN = 1209226
O
O
XRN = 1720409
Identification (21)
Physical Data (16)
Spectra (10)
Use/Application (1)
Identification (12)
Physical Data (16)
Spectra (16)
Bioactivity/Ecotox (4)
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Use/Application (1)
Natural Product (1)
O
O
XRN = 1740720
P
O
O
O
O
O
XRN = 1789280
Identification (59)
Physical Data (148)
Spectra (64)
Bioactivity/Ecotox (5)
Natural Product (1)
Identification (11)
Physical Data (15)
Spectra (11)
O
XRN = 1861022
XRN = 1930011
Identification (18)
Physical Data (25)
Spectra (34)
Identification (9)
Physical Data (6)
Spectra (8)
O
XRN = 1939796
HO
O
XRN = 1943807
Identification (19)
Physical Data (19)
Spectra (17)
Identification (22)
Physical Data (13)
Spectra (8)
HO
O
E
XRN = 1945305
HO
O
XRN = 1947465
Identification (6)
Physical Data (17)
Spectra (12)
Natural Product (1)
Identification (15)
Physical Data (16)
Spectra (10)
OH
O
XRN = 1947864
HO
O
XRN = 1950675
Identification (23)
Physical Data (17)
Spectra (5)
Bioactivity/Ecotox (1)
Identification (5)
Physical Data (3)
O
S
OH
HO O
XRN = 2037554
XRN = 2039922
Identification (29)
Physical Data (1676)
Spectra (87)
Bioactivity/Ecotox (1)
Use/Application (219)
Identification (17)
Physical Data (23)
Spectra (15)
Bioactivity/Ecotox (1)
HO
O
E
XRN = 2042546
O
XRN = 2043573
Identification (42)
Physical Data (38)
Spectra (28)
Bioactivity/Ecotox (3)
Identification (51)
Physical Data (45)
Spectra (53)
Bioactivity/Ecotox (1)
Cl
XRN = 2087646
O
XRN = 2088577
Identification (5)
Physical Data (1)
Identification (5)
Physical Data (1)
O
Cl
XRN = 2089977
O
XRN = 2091390
Identification (5)
Physical Data (1)
Spectra (1)
Identification (5)
Physical Data (1)
HO
O
XRN = 2091743
O
XRN = 2092649
Identification (5)
Physical Data (3)
Identification (5)
Physical Data (1)
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O
Cl
XRN = 2096388
O
O
XRN = 2097005
Identification (5)
Physical Data (1)
Identification (5)
Physical Data (3)
HO
O
Cl
XRN = 2097056
O
O
XRN = 2097474
Identification (7)
Physical Data (1)
Identification (5)
Physical Data (1)
N
XRN = 2098135
O
O
XRN = 2099826
Identification (6)
Physical Data (2)
Identification (5)
Physical Data (1)
HO
O
Cl
XRN = 2101483
HO
O
XRN = 2101798
Identification (4)
Physical Data (1)
Bioactivity/Ecotox (1)
Identification (5)
Physical Data (2)
O
O
Cl
XRN = 2102439
O
O
Cl
XRN = 2103954
Identification (8)
Physical Data (4)
Spectra (6)
Identification (5)
Physical Data (1)
HO
O
XRN = 2104396
HO
O
Cl
XRN = 2108075
Identification (5)
Physical Data (1)
Identification (5)
Physical Data (1)
HO O
XRN = 2111727
HO
O
XRN = 2116018
Identification (6)
Physical Data (1)
Identification (6)
HO O
XRN = 2118172
HO O
XRN = 2119624
Identification (5)
Physical Data (1)
Identification (6)
Physical Data (1)
O
O
XRN = 2120454
XRN = 2205890
Identification (4)
Physical Data (1)
Identification (7)
Physical Data (4)
O
O
XRN = 2209134
O
O
XRN = 2210249
Identification (15)
Physical Data (12)
Spectra (15)
Identification (5)
Physical Data (1)
Spectra (6)
HO
O
XRN = 2210746
HO
O
XRN = 2211625
Identification (9)
Physical Data (1)
Spectra (1)
Identification (10)
Physical Data (2)
Spectra (1)
HO
O
XRN = 2212093
O
O
XRN = 2212298
Identification (10)
Physical Data (2)
Spectra (1)
Identification (15)
Physical Data (11)
Spectra (5)
Copyright © 2011 Elsevier Properties SA. All rights reserved. Authorized use only.
Reaxys ® is a trademark owned and protected by Elsevier Properties SA and used
under license.
30/43
2011-06-13 13:28:23
Cl
HO O
XRN = 2212457
HO
O
XRN = 2212686
Identification (6)
Physical Data (1)
Identification (8)
Physical Data (2)
HO
O
XRN = 2213760
HO
O
XRN = 2214042
Identification (12)
Physical Data (3)
Bioactivity/Ecotox (4)
Identification (8)
Physical Data (4)
Spectra (1)
HO
O
XRN = 2214599
HO
O
XRN = 2214602
Identification (8)
Physical Data (3)
Spectra (1)
Identification (13)
Physical Data (2)
Cl
HO O
XRN = 2214944
Cl
HO O
XRN = 2216914
Identification (7)
Physical Data (1)
Identification (6)
Physical Data (1)
Cl
HO O
XRN = 2216977
Cl
XRN = 2255380
Identification (7)
Identification (4)
Physical Data (1)
O
HO
O
XRN = 2646872
HO
HO
O
XRN = 2647517
Identification (6)
Physical Data (2)
Identification (5)
Physical Data (2)
Spectra (1)
HO
HO
O
XRN = 2649721
HO
HO
O
XRN = 2650897
Identification (4)
Identification (6)
Physical Data (2)
O
O
O
XRN = 2657647
O
O O
XRN = 2846664
Identification (4)
Identification (5)
Physical Data (1)
O
O
O
XRN = 2848716
Cl
O
O O
XRN = 2851542
Identification (5)
Physical Data (1)
Identification (5)
Physical Data (1)
O
O
O
XRN = 2854132
O
O O
XRN = 2857592
Identification (5)
Physical Data (1)
Identification (4)
Physical Data (1)
HO
O
XRN = 3263263
HO
O
XRN = 3322584
Identification (3)
Physical Data (3)
Identification (4)
Physical Data (1)
Copyright © 2011 Elsevier Properties SA. All rights reserved. Authorized use only.
Reaxys ® is a trademark owned and protected by Elsevier Properties SA and used
under license.
31/43
2011-06-13 13:28:23
O
–
O
Hg
2+
(v0)
2
XRN = 3563831
HO
O
XRN = 4137341
Identification (22)
Physical Data (121)
Spectra (31)
Bioactivity/Ecotox (1)
Use/Application (7)
Identification (4)
HO
O
E
XRN = 5928876
HO
O
Cl
E
XRN = 6720175
Identification (4)
Physical Data (1)
Spectra (1)
Identification (4)
No Structure
XRN = 13294607
HO
XRN = 13313549
Physical Data (1)
Identification (3)
O
O
O
XRN = 13314528
OH
O
XRN = 13314877
Identification (3)
Physical Data (1)
Identification (4)
HO
HO
O
XRN = 13314926
OH
O
XRN = 13314984
Identification (3)
Identification (4)
HO
O
O
XRN = 13315030
HO
HO
O
XRN = 13315073
Identification (3)
Identification (3)
Cl
O
O
XRN = 13315202
HO
O
O
XRN = 13315267
Identification (3)
Physical Data (2)
Identification (3)
OH
HO
O
XRN = 13315546
Cl
Cl
OH
O
XRN = 13315758
Identification (3)
Identification (4)
Cl
OH
O
XRN = 13315764
Cl
Cl
OH
O
XRN = 13315774
Identification (4)
Identification (4)
OH
HO
O
Cl
XRN = 13315807
No Structure
XRN = 14803695
Identification (3)
XRN = 15316078
HO
O
XRN = 15316110
Identification (3)
Identification (3)
Copyright © 2011 Elsevier Properties SA. All rights reserved. Authorized use only.
Reaxys ® is a trademark owned and protected by Elsevier Properties SA and used
under license.
32/43
2011-06-13 13:28:23
Cl
O
O
O
XRN = 15316369
Identification (3)
Copyright © 2011 Elsevier Properties SA. All rights reserved. Authorized use only.
Reaxys ® is a trademark owned and protected by Elsevier Properties SA and used
under license.
33/43
2011-06-13 13:28:23
Sandoz AG
Patent: FR2248831; (1974)
Chem.Abstr.; vol. 83; nb. 192925
reaction 1 of 6 / citation 3 of 4
O
Yield
Conditions & References
reaction 2 of 6 / citation 3 of 4
O
O
Yield
Conditions & References
reaction 3 of 6 / citation 3 of 4
HO
O
Yield
Conditions & References
reaction 4 of 6 / citation 3 of 4
HO O
Yield
Conditions & References
reaction 5 of 6 / citation 3 of 4
HO
O
Yield
Conditions & References
α-Hydroxy-Verb., H2
reaction 6 of 6 / citation 3 of 4
O
O
Yield
Conditions & References
Copyright © 2011 Elsevier Properties SA. All rights reserved. Authorized use only.
Reaxys ® is a trademark owned and protected by Elsevier Properties SA and used
under license.
34/43
2011-06-13 13:28:23
O
XRN = 2091390
O
O
XRN = 2099826
Identification (5)
Physical Data (1)
Identification (5)
Physical Data (1)
HO
O
XRN = 2101798
HO O
XRN = 2111727
Identification (5)
Physical Data (2)
Identification (6)
Physical Data (1)
HO
O
XRN = 2116018
O
O
XRN = 2210249
Identification (6)
Identification (5)
Physical Data (1)
Spectra (6)
Copyright © 2011 Elsevier Properties SA. All rights reserved. Authorized use only.
Reaxys ® is a trademark owned and protected by Elsevier Properties SA and used
under license.
35/43
2011-06-13 13:28:23
Sandoz AG
Patent: CH592598; (1973)
DE2449928
Chem.Abstr.; vol. 83; nb. 192925
reaction 1 of 41 / citation 4 of 4
O
Yield
Conditions & References
reaction 2 of 41 / citation 4 of 4
HO
O
Yield
Conditions & References
reaction 3 of 41 / citation 4 of 4
HO
O
Cl
Yield
Conditions & References
reaction 4 of 41 / citation 4 of 4
HO
O
Yield
Conditions & References
reaction 5 of 41 / citation 4 of 4
O
Yield
Conditions & References
reaction 6 of 41 / citation 4 of 4
Yield
Conditions & References
Copyright © 2011 Elsevier Properties SA. All rights reserved. Authorized use only.
Reaxys ® is a trademark owned and protected by Elsevier Properties SA and used
under license.
36/43
2011-06-13 13:28:23
reaction 7 of 41 / citation 4 of 4
Cl
Yield
Conditions & References
reaction 8 of 41 / citation 4 of 4
Cl
Yield
Conditions & References
reaction 9 of 41 / citation 4 of 4
O
Yield
Conditions & References
reaction 10 of 41 / citation 4 of 4
O
Cl
Yield
Conditions & References
reaction 11 of 41 / citation 4 of 4
O
Cl
Yield
Conditions & References
reaction 12 of 41 / citation 4 of 4
HO
O
Cl
Yield
Conditions & References
reaction 13 of 41 / citation 4 of 4
O
O
Yield
Conditions & References
Copyright © 2011 Elsevier Properties SA. All rights reserved. Authorized use only.
Reaxys ® is a trademark owned and protected by Elsevier Properties SA and used
under license.
37/43
2011-06-13 13:28:23
reaction 14 of 41 / citation 4 of 4
HO
O
Cl
Yield
Conditions & References
reaction 15 of 41 / citation 4 of 4
O
O
Cl
Yield
Conditions & References
reaction 16 of 41 / citation 4 of 4
O
O
Cl
Yield
Conditions & References
reaction 17 of 41 / citation 4 of 4
HO
O
Cl
Yield
Conditions & References
reaction 18 of 41 / citation 4 of 4
Yield
Conditions & References
reaction 19 of 41 / citation 4 of 4
O
O
Yield
Conditions & References
reaction 20 of 41 / citation 4 of 4
O
O
Yield
Conditions & References
Copyright © 2011 Elsevier Properties SA. All rights reserved. Authorized use only.
Reaxys ® is a trademark owned and protected by Elsevier Properties SA and used
under license.
38/43
2011-06-13 13:28:23
reaction 21 of 41 / citation 4 of 4
HO
O
Yield
Conditions & References
entspr. Nitril, KOH
reaction 22 of 41 / citation 4 of 4
HO
O
Yield
Conditions & References
entspr. Nitril, KOH
reaction 23 of 41 / citation 4 of 4
HO
O
Yield
Conditions & References
entspr. Nitril, KOH
reaction 24 of 41 / citation 4 of 4
O
O
Yield
Conditions & References
entspr. Saeure, Me.
reaction 25 of 41 / citation 4 of 4
Cl
HO O
Yield
Conditions & References
entspr. Nitril, KOH
reaction 26 of 41 / citation 4 of 4
HO
O
Yield
Conditions & References
entspr. Nitril, KOH
Copyright © 2011 Elsevier Properties SA. All rights reserved. Authorized use only.
Reaxys ® is a trademark owned and protected by Elsevier Properties SA and used
under license.
39/43
2011-06-13 13:28:23
reaction 27 of 41 / citation 4 of 4
HO
O
Yield
Conditions & References
entspr. Nitril, KOH
reaction 28 of 41 / citation 4 of 4
HO
O
Yield
Conditions & References
entspr. 5-Acetonitril, KOH
reaction 29 of 41 / citation 4 of 4
HO
O
Yield
Conditions & References
entspr. Nitril, KOH
reaction 30 of 41 / citation 4 of 4
HO
O
Yield
Conditions & References
entspr. Nitril, KOH
reaction 31 of 41 / citation 4 of 4
Cl
HO O
Yield
Conditions & References
entspr. Nitril, KOH
reaction 32 of 41 / citation 4 of 4
Cl
HO O
Yield
Conditions & References
entspr. Nitril, KOH
Copyright © 2011 Elsevier Properties SA. All rights reserved. Authorized use only.
Reaxys ® is a trademark owned and protected by Elsevier Properties SA and used
under license.
40/43
2011-06-13 13:28:23
reaction 33 of 41 / citation 4 of 4
Cl
HO O
Yield
Conditions & References
entspr. Nitril, KOH
reaction 34 of 41 / citation 4 of 4
H
2
N
HO
O
Yield
Conditions & References
reaction 35 of 41 / citation 4 of 4
H
2
N
HO
O
Yield
Conditions & References
reaction 36 of 41 / citation 4 of 4
H
2
N
HO
O
Yield
Conditions & References
reaction 37 of 41 / citation 4 of 4
H
2
N
HO
O
Yield
Conditions & References
reaction 38 of 41 / citation 4 of 4
H
2
N
HO
O
Yield
Conditions & References
reaction 39 of 41 / citation 4 of 4
H
2
N
HO
OH
OH
HO
O
Yield
Conditions & References
Copyright © 2011 Elsevier Properties SA. All rights reserved. Authorized use only.
Reaxys ® is a trademark owned and protected by Elsevier Properties SA and used
under license.
41/43
2011-06-13 13:28:23
reaction 40 of 41 / citation 4 of 4
H
2
N
Cl
HO O
Yield
Conditions & References
reaction 41 of 41 / citation 4 of 4
H
2
N
HO
OH
OH
HO
O
Yield
Conditions & References
entspr. Nitril, KOH
O
XRN = 1861022
HO
O
XRN = 1943807
Identification (18)
Physical Data (25)
Spectra (34)
Identification (22)
Physical Data (13)
Spectra (8)
HO
O
Cl
XRN = 1955847
HO
O
XRN = 2042544
Identification (5)
Physical Data (5)
Spectra (2)
Use/Application (1)
Identification (21)
Physical Data (29)
Spectra (9)
Use/Application (1)
O
XRN = 2043573
XRN = 2076897
Identification (51)
Physical Data (45)
Spectra (53)
Bioactivity/Ecotox (1)
Identification (4)
Physical Data (9)
Cl
XRN = 2080189
Cl
XRN = 2087646
Identification (4)
Physical Data (1)
Identification (5)
Physical Data (1)
O
XRN = 2088577
O
Cl
XRN = 2089977
Identification (5)
Physical Data (1)
Identification (5)
Physical Data (1)
Spectra (1)
O
Cl
XRN = 2096388
HO
O
Cl
XRN = 2097056
Identification (5)
Physical Data (1)
Identification (7)
Physical Data (1)
O
O
XRN = 2097474
HO
O
Cl
XRN = 2101483
Identification (5)
Physical Data (1)
Identification (4)
Physical Data (1)
Bioactivity/Ecotox (1)
O
O
Cl
XRN = 2102439
O
O
Cl
XRN = 2103954
Identification (8)
Physical Data (4)
Identification (5)
Physical Data (1)
Copyright © 2011 Elsevier Properties SA. All rights reserved. Authorized use only.
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under license.
42/43
2011-06-13 13:28:23
Spectra (6)
HO
O
Cl
XRN = 2108075
XRN = 2205890
Identification (5)
Physical Data (1)
Identification (7)
Physical Data (4)
O
O
XRN = 2209134
O
O
XRN = 2210249
Identification (15)
Physical Data (12)
Spectra (15)
Identification (5)
Physical Data (1)
Spectra (6)
HO
O
XRN = 2210746
HO
O
XRN = 2211625
Identification (9)
Physical Data (1)
Spectra (1)
Identification (10)
Physical Data (2)
Spectra (1)
HO
O
XRN = 2212093
O
O
XRN = 2212298
Identification (10)
Physical Data (2)
Spectra (1)
Identification (15)
Physical Data (11)
Spectra (5)
Cl
HO O
XRN = 2212457
HO
O
XRN = 2212686
Identification (6)
Physical Data (1)
Identification (8)
Physical Data (2)
HO
O
XRN = 2213760
HO
O
XRN = 2214042
Identification (12)
Physical Data (3)
Bioactivity/Ecotox (4)
Identification (8)
Physical Data (4)
Spectra (1)
HO
O
XRN = 2214599
HO
O
XRN = 2214602
Identification (8)
Physical Data (3)
Spectra (1)
Identification (13)
Physical Data (2)
Cl
HO O
XRN = 2214944
Cl
HO O
XRN = 2216914
Identification (7)
Physical Data (1)
Identification (6)
Physical Data (1)
Cl
HO O
XRN = 2216977
H
2
N
HO
O
XRN = 4050302
Identification (7)
Identification (4)
Physical Data (1)
H
2
N
HO
O
XRN = 4051822
H
2
N
HO
O
XRN = 4052598
Identification (4)
Physical Data (1)
Identification (4)
Physical Data (1)
H
2
N
HO
O
XRN = 4054150
H
2
N
HO
O
XRN = 4058383
Identification (4)
Physical Data (1)
Identification (4)
Physical Data (1)
Copyright © 2011 Elsevier Properties SA. All rights reserved. Authorized use only.
Reaxys ® is a trademark owned and protected by Elsevier Properties SA and used
under license.
43/43
2011-06-13 13:28:23
H
2
N
HO
OH
OH
HO
O
XRN = 4061961
H
2
N
Cl
HO O
XRN = 4066873
Identification (4)
Physical Data (1)
Identification (4)
Physical Data (1)
H
2
N
HO
OH
OH
HO
O
XRN = 4170512
Identification (5)
Physical Data (1)
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