US3975431A
Expired / Lapsed
US
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Preparing carboxylic acids from glycidonitriles through enol acylates
Assignee: Pharmacia and Upjohn Co
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Filing: 1974-12-10
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Granted: 1976-08-17
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Expires: 1994-12-10
Abstract
Abstract Process for preparing carboxylic acids by converting a glycidonitrile to the enol acylate via hydrohalogenation, acylation and dehydrohalogenation procedures, and conversion of the enol acylate to the carboxylate salt with a base and of the salt to the carboxylic acid with acid. Cyanide content in the mixture is destroyed by adding persulfate or hypochlorite salts. This process, can be used, e.g., to prepare 2-(4'-isobutylphenyl)propionic acid, now known generically as ibuprofen, a highly active anti-inflammatory drug, as well as a host of other useful carboxylic acids.
Inventors
- 👤 David R. White
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 22:38
CPC Classifications
C; C07; C07J; C07J1/00; C07J1/0003; C07J1/0018; C07J1/0022; C07J1/0025; C07C; C07C51/00; C07C51/08; C07D; C07D303/00; C07D303/02; C07D303/48
Claims Analysis
Total Claims: 4
Claim 1
Independent Claim
236 words
The process for the production of a carboxylic acid of the formula: ##EQU3## wherein R when taken separately represents hydrogen or an aliphatic, or aromatic group and R 1 when taken separately represents an aliphatic or aromatic group; and R and R 1 when taken together and connected represents an alicyclic group, which comprises: 1. treating a glycidonitrile of the formula: ##EQU4## wherein R and R 1 have the meaning given, above, with a hydrogen halide selected from the group consisting of hydrogen chloride, hydrogen bromide and hydrogen iodide to obtain a 2-hydroxy-3-halopropionitrile of the formula: ##EQU5## wherein R and R 1 have the meanings given, above, and X is selected from the group consisting of chloro, bromo, and iodo; 2. acylating and dehydrohalogenating the 2-hydroxy-3-halopropionitrile thus obtained to obtain an enol acylate of the formula: ##EQU6## wherein R and R 1 have the meanings given, above, and R 2 is the acyl radical of an organic carboxylic acid; 3. subjecting the enol acylate so obtained to hydrolysis with an aqueous alkali metal base to obtain an alkali metal salt of a carboxylic acid of the formula: ##EQU7## wherein R and R 1 have the meanings given, above, and M + is selected from the group consisting of sodium, potassium, and lithium, and 4. acidifying the alkali metal salt of the carboxylic acid so obtained with a strong acid to obtain the corresponding free carboxylic acid.
Claim 2
Dependent Claim
236 words
The process for the production of a carboxylic acid of the formula: ##EQU3## wherein R when taken separately represents hydrogen or an aliphatic, or aromatic group and R 1 when taken separately represents an aliphatic or aromatic group; and R and R 1 when taken together and connected represents an alicyclic group, which comprises: 1. treating a glycidonitrile of the formula: ##EQU4## wherein R and R 1 have the meaning given, above, with a hydrogen halide selected from the group consisting of hydrogen chloride, hydrogen bromide and hydrogen iodide to obtain a 2-hydroxy-3-halopropionitrile of the formula: ##EQU5## wherein R and R 1 have the meanings given, above, and X is selected from the group consisting of chloro, bromo, and iodo; 2. acylating and dehydrohalogenating the 2-hydroxy-3-halopropionitrile thus obtained to obtain an enol acylate of the formula: ##EQU6## wherein R and R 1 have the meanings given, above, and R 2 is the acyl radical of an organic carboxylic acid; 3. subjecting the enol acylate so obtained to hydrolysis with an aqueous alkali metal base to obtain an alkali metal salt of a carboxylic acid of the formula: ##EQU7## wherein R and R 1 have the meanings given, above, and M + is selected from the group consisting of sodium, potassium, and lithium, and 4. acidifying the alkali metal salt of the carboxylic acid so obtained with a strong acid to obtain the corresponding free carboxylic acid.
Claim 3
Dependent Claim
15 words
Process in accordance with claim 1 wherein R is aromatic and R 1 is aliphatic.
Claim 4
Dependent Claim
91 words
Process in accordance with claim 2 for the production of 2-(p-isobutylphenyl)-propionic acid which comprises: 1. treating 3-methyl-3-(p-isobutylphenyl)glycidonitrile with a hydrogen halide selected from the group consisting of hydrogen chloride, hydrogen bromide and hydrogen iodide, to obtain the corresponding 2-hydroxy-3-methyl-3-(p-isobutylphenyl)-3-halopropionitrile; 2. acylating and dehydrohalogenating the 2-hydroxy-3-methyl-3-(p-isobutylphenyl)-3-halopropionitrile thus obtained to produce the corresponding 2-acryloxy-3-methyl-3-(p-isobutylphenyl)acrylonitrile; 3. subjecting the 2-acyloxy-3-methyl-3-(p-isobutylphenyl)acrylonitrile thus produced to hydrolysis with an aqueous alkali metal base to obtain the corresponding alkali metal salt of 2-(p-isobutylphenyl)propionic acid; and 4. acidifying the salt thus obtained with a strong acid to produce 2-(p-isobutylphenyl)propionic acid.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-08-17 | 1980-02-16 | 1980-08-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-17 | 1984-02-16 | 1984-08-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-17 | 1988-02-16 | 1988-08-17 | $7700.00 | Window Closed / Lapsed |