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US 4,268,442 AGranted
Process for preparing aromatic acetic acid
AssigneeSagami Chemical Research Center
InventorsKiyosi Kondo, Tamotsu Fujimoto, Minoru Suda, Daiei Tunemoto
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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.
Claims22
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.sup.1 and R.sup.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.sup.1 and R.sup.2 may cooperate to form a lower alkylidenedioxy group;
- (b) a group of the formula:
- ##STR19## wherein R.sup.1 and R.sup.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.sup.6 group in which R.sup.6 is a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, and R.sup.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.
12 more elements
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.sup.1 and R.sup.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.sup.1 and R.sup.2 may cooperate to form a lower alkylidenedioxy group;
- (b) a group of the formula:
- ##STR23## wherein R.sup.1 and R.sup.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.sup.6 group in which R.sup.6 is a hydrogen atom or a lower alkyl group having from 1 to 4 carbon atoms, and R.sup.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.
10 more elements
Dependencies are inferred from the claim text.