US4268442A
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Process for preparing aromatic acetic acid
Assignee: Sagami Chemical Research Institute
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Filing: 1979-11-13
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Granted: 1981-05-19
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Expires: 1999-11-13
Abstract
Abstract There are disclosed processes for preparing an aromatic acetic acid by the reaction of an aromatic aldehyde with a combination of a trihalomethane and an alkanethiol, and by the reaction of an alcohol derivative (2,2,2-trihalo-1-arylethanol) with an alkanethiol, in the presence of a base in a mixed medium of water and an aprotic polar solvent.
Inventors
- 👤 Kiyosi Kondo
- 👤 Tamotsu Fujimoto
- 👤 Minoru Suda
- 👤 Daiei Tunemoto
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 10:12
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/30; C07D207/32; C07D207/33; C07D207/337; C07C; C07C323/00; C07C51/00; C07C51/093; C07D317/00; C07D317/08; C07D317/44; C07D317/46; C07D317/48; C07D317/50; C07D317/60; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/24
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
302 words
A process for preparing an aromatic acetic acid represented by the formula ArCH.sub.2 COOH wherein Ar is a substituted or unsubstituted aromatic selected from the group consisting of the following groups (a), (b) and (c): (a) a group of the formula ##STR18## wherein R 1 and R 2 may be at the same or different and each represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a phenoxy group, a benzyloxy group or R 1 and R 2 may cooperate to form a lower alkylidenedioxy group; (b) a group of the formula: ##STR19## wherein R 1 and R 2 are the same as defined above; and (c) a group of the formula ##STR20## wherein A represents an oxygen atom (O), a sulfur atom (S) or a >NR 6 group in which R 6 is a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, and R 3 represents a hydrogen atom or a lower alkyl substituted benzoyl group; which comprises reacting an aromatic aldehyde represented by the formula ArCHO wherein Ar has the same meaning as defined above, with a trihalomethane represented by the formula HCX.sub.3 wherein X represents at least one halogen selected from the group consisting of chlorine and bromine atoms, in the presence of a base in a mixed medium of water and an aprotic polar solvent to form an alcohol derivative represented by the formula ##STR21## wherein Ar has the same medium as defined above, and then reacting the thus formed alcohol derivative with an alkanethiol represented by the formula RSH wherein R is an alkyl group, in the presence of a base in a mixed medium of water and an aprotic polar solvent, wherein the volume ratio of said water and said aprotic polar solvent is 1:0.2-1:5.
Claim 2
Dependent Claim
302 words
A process for preparing an aromatic acetic acid represented by the formula ArCH.sub.2 COOH wherein Ar is a substituted or unsubstituted aromatic selected from the group consisting of the following groups (a), (b) and (c): (a) a group of the formula ##STR18## wherein R 1 and R 2 may be at the same or different and each represent a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a phenoxy group, a benzyloxy group or R 1 and R 2 may cooperate to form a lower alkylidenedioxy group; (b) a group of the formula: ##STR19## wherein R 1 and R 2 are the same as defined above; and (c) a group of the formula ##STR20## wherein A represents an oxygen atom (O), a sulfur atom (S) or a >NR 6 group in which R 6 is a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, and R 3 represents a hydrogen atom or a lower alkyl substituted benzoyl group; which comprises reacting an aromatic aldehyde represented by the formula ArCHO wherein Ar has the same meaning as defined above, with a trihalomethane represented by the formula HCX.sub.3 wherein X represents at least one halogen selected from the group consisting of chlorine and bromine atoms, in the presence of a base in a mixed medium of water and an aprotic polar solvent to form an alcohol derivative represented by the formula ##STR21## wherein Ar has the same medium as defined above, and then reacting the thus formed alcohol derivative with an alkanethiol represented by the formula RSH wherein R is an alkyl group, in the presence of a base in a mixed medium of water and an aprotic polar solvent, wherein the volume ratio of said water and said aprotic polar solvent is 1:0.2-1:5.
Claim 3
Dependent Claim
18 words
A process according to claim 1 wherein said reaction is carried out without isolation of said alcohol derivative.
Claim 4
Dependent Claim
28 words
A process according to claim 1 or 2 wherein said base is used in an amount of 4 to 8 molar equivalents with respect to said aromatic aldehyde.
Claim 5
Dependent Claim
22 words
A process according to claim 1 or 2 wherein the volume ratio of said water and said aprotic polar solvent is 1:0.8-1:1.2.
Claim 6
Dependent Claim
16 words
A process according to claim 1 or 2 wherein said base is an alkali metal hydroxide.
Claim 7
Dependent Claim
21 words
A process according to claim 1 or 2 wherein R is a lower alkyl group having 1 to 4 carbon atoms.
Claim 8
Dependent Claim
18 words
A process according to claim 1 or 2 wherein said aprotic polar solvent is dimethyl sulfoxide or acetonitrile.
Claim 9
Dependent Claim
241 words
A process for preparting an aromatic acetic acid represented by the formula ArCH.sub.2 COOH wherein Ar represents a substituted or unsubstituted aromatic group selected from the group consisting of the following groups (a), (b) and (c): (a) a group of the formula: ##STR22## wherein R 1 and R 2 may be the same or different and each represent a hydrogen atom, a lower akyl group, a lower alkoxy group, a halogen atom, a phenoxy group, a benzyloxy group or R 1 and R 2 may cooperate to form a lower alkylidenedioxy group; (b) a group of the formula: ##STR23## wherein R 1 and R 2 are the same as defined above; and (c) a group of the formula: ##STR24## wherein A represents an oxygen atom (O), a sulfur atom (S) or a >NR 6 group in which R 6 is a hydrogen atom or a lower alkyl group having from 1 to 4 carbon atoms, and R 3 a represents a hydrogen atom or a lower alkyl substituted benzoyl group; which comprises reacting an alcohol derivative represented by the formula ##STR25## wherein Ar has the same meaning as defined above, and X represents a halogen atom, with an alkanethiol represented by the formula RSH wherein R represents an alkyl group, in the presence of a base in a mixed medium of water and an aprotic polar solvent, wherein the volume ratio of said water and said aprotic polar solvent is 1:0.2-1:5.
Claim 10
Dependent Claim
241 words
A process for preparting an aromatic acetic acid represented by the formula ArCH.sub.2 COOH wherein Ar represents a substituted or unsubstituted aromatic group selected from the group consisting of the following groups (a), (b) and (c): (a) a group of the formula: ##STR22## wherein R 1 and R 2 may be the same or different and each represent a hydrogen atom, a lower akyl group, a lower alkoxy group, a halogen atom, a phenoxy group, a benzyloxy group or R 1 and R 2 may cooperate to form a lower alkylidenedioxy group; (b) a group of the formula: ##STR23## wherein R 1 and R 2 are the same as defined above; and (c) a group of the formula: ##STR24## wherein A represents an oxygen atom (O), a sulfur atom (S) or a >NR 6 group in which R 6 is a hydrogen atom or a lower alkyl group having from 1 to 4 carbon atoms, and R 3 a represents a hydrogen atom or a lower alkyl substituted benzoyl group; which comprises reacting an alcohol derivative represented by the formula ##STR25## wherein Ar has the same meaning as defined above, and X represents a halogen atom, with an alkanethiol represented by the formula RSH wherein R represents an alkyl group, in the presence of a base in a mixed medium of water and an aprotic polar solvent, wherein the volume ratio of said water and said aprotic polar solvent is 1:0.2-1:5.
Claim 11
Dependent Claim
26 words
A process according to claim 8 wherein said base is used in an amount of 4 to 8 molar equivalents with respect to said alcohol derivative.
Claim 12
Dependent Claim
22 words
A process according to claim 8 or 9 wherein the volume ratio of said water and said aprotic polar solvent is 1:0.8-1:12.
Claim 13
Dependent Claim
16 words
A process according to claim 8 or 9 wherein said base is an alkali metal hydroxide.
Claim 14
Dependent Claim
21 words
A process according to claim 8 or 9 wherein R is a lower alkyl group having 1 to 4 carbon atoms.
Claim 15
Dependent Claim
18 words
A process according to claim 8 or 9 wherein said aprotic polar solvent is dimethyl sulfoxide or acetonitrile.
Claim 16
Dependent Claim
19 words
A process according to claim 10, wherein R is a lower alkyl group having 1 to 4 carbon atoms.
Claim 17
Dependent Claim
14 words
A process according to claim 14, wherein said base is an alkali metal hydroxide.
Claim 18
Dependent Claim
16 words
A process according to claim 15, wherein said aprotic polar solvent is dimethyl sulfoxide or acetonitrile.
Claim 19
Dependent Claim
16 words
A process according to claim 10, wherein said aprotic polar solvent is dimethyl sulfoxide or acetonitrile.
Claim 20
Dependent Claim
19 words
A process according to claim 4, wherein R is a lower alkyl group having 1 to 4 carbon atoms.
Claim 21
Dependent Claim
14 words
A process according to claim 18, wherein said base is an alkali metal hydroxide.
Claim 22
Dependent Claim
16 words
A process according to claim 19, wherein said aprotic polar solvent is dimethyl sulfoxide or acetonitrile.
Claim 23
Dependent Claim
16 words
A process according to claim 4, wherein said aprotic polar solvent is dimethyl sulfoxide or acetonitrile.
Claim 24
Dependent Claim
17 words
The process of claim 1 or 8, wherein said aromatic group is a chloro- or bromo-substituted group.
References Cited (Backward Citations)
DE2810262A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-05-18 | 1984-11-17 | 1985-05-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-05-18 | 1988-11-17 | 1989-05-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-05-18 | 1992-11-17 | 1993-05-19 | $7700.00 | Window Closed / Lapsed |