# US 4,393,233 A · Preparation of p-(1,1-dimethyl-2-hydroxyethyl)benzoic acid

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- Number: US 4,393,233 A
- Document ID: US4393233A
- Status: Granted
- Kind: A
- Application number: 06/337,900
- Filed: 1982-01-07
- Granted: 1983-07-12
- Earliest claimed: 1980-05-27
- Assignees: Allied Corporation
- Inventors: Herbert K. Reimschuessel; Bruce T. DeBona
- Web page: https://patentgrep.com/patent/US4393233A

## CPC

- C08G 63/664: derived from hydroxy carboxylic acids
- C07C 51/08: from nitriles
- C07C 51/29: with halogen-containing compounds which may be formed in situ
- C07C 51/353: by isomerisation; by change of size of the carbon skeleton
- C07C 51/363: by introduction of halogen; by substitution of halogen atoms by other halogen atoms
- C08G 63/06: derived from hydroxycarboxylic acids
- C08G 63/065: {the hydroxy and carboxylic ester groups being bound to aromatic rings}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The subject polymers are novel homopolymers and copolymers. The homopolymers are characterized by relatively high T.sub.g of about 120.degree. C. relative to their T.sub.m of about 250.degree. C., whereby they can readily be fabricated into fibers, films and like structures from the melt, and retain strength above 100.degree. C. The copolymers have T.sub.g 's intermediate between those of the homopolymers of the constituent monomers, and can be fabricated as for the subject homopolymers. Novel processes of obtaining the monomer, p-(1,1-dimethyl-2-hydroxyethyl)benzoic acid, are disclosed.

## Claims

### Claim 1

Process for production of (p-1,1-dimethyl-2-hydroxyethyl)benzoic acid comprising the steps:
(a) Brominating isobutyric acid;
(b) Condensing the resulting alpha-bromoisobutyric acid with benzene;
(c) Brominating the resulting dimethylphenylacetic acid;
(d) Reducing the carboxyl group of the brominated acid obtained in step (c) to form p-(1,1-dimethyl-1-hydroxyethyl)bromobenzene;
(e) Replacing the bromine atom in the product obtained in step (d) by the cyano group;
(f) Converting the cyano group in the product of step (e) to the carboxyl group.

### Claim 2

Process for production of (p-1,1-dimethyl-2-hydroxyethyl)benzoic acid comprising the steps:
(a) p-Acetylating beta,beta-dimethylphenethyl acetate;
(b) Oxidizing the acetyl group in the product of step (a) to carboxyl and converting the ester group to hydroxyl, to form (p-1,1-dimethyl-2-hydroxyethyl)benzoic acid.