US3965161A
Expired / Lapsed
US
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Process of producing a 2-(4-alkylphenyl)-propionic acid
Assignee: Nisshin Seifun Group Inc
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Filing: 1974-01-25
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Granted: 1976-06-22
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Expires: 1994-01-25
Abstract
Abstract A new process of producing a 2-(4-alkylphenyl)-propionic acid known as a valuable anti-inflammatory agent is now provided, which comprises treating an alkyl 3-methyl-3-(4-alkylphenyl)-glycidate with an acid to produce 2-(4-alkylphenyl)-propionaldehyde and 3-methyl-3-(4-alkylphenyl)-pyruvic acid through a new reaction, and then oxidising these intermediate products to the desired 2-(4-alkylphenyl)-propionic acid. This new process is operable in a facile way, gives a high yield of the desired product and is suitable for a commercial practice.
Inventors
- 👤 Katsura Kogure
- 👤 Kunio Nakagawa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 21:13
CPC Classifications
C; C07; C07D; C07D303/00; C07D303/02; C07D303/48; C07C; C07C45/00; C07C45/56; C07C45/57; C07C45/58; C07C51/00; C07C51/16; C07C51/347; C07C51/373; C07C57/00; C07C57/30; C07C59/00; C07C59/40; C07C59/76; C07C59/84
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
20 words
A single-stage process for converting a 3-methyl-3-(4-alkylphenyl)-glycidic acid alkyl ester into a 2-(4-alkylphenyl)-propionaldehyde and a 3-methyl-3-(4-alkylphenyl)-pyruvic acid, which comprises treating:
Claim 2
Dependent Claim
20 words
A single-stage process for converting a 3-methyl-3-(4-alkylphenyl)-glycidic acid alkyl ester into a 2-(4-alkylphenyl)-propionaldehyde and a 3-methyl-3-(4-alkylphenyl)-pyruvic acid, which comprises treating:
Claim 3
Dependent Claim
29 words
a. a 3-methyl-3-(4-alkylphenyl)-glycidic acid alkyl ester of the formula ##SPC16## wherein R 1 is alkyl of 2-4 carbon atoms and R 2 is alkyl of 1-4 carbon atoms, with
Claim 4
Dependent Claim
29 words
a. a 3-methyl-3-(4-alkylphenyl)-glycidic acid alkyl ester of the formula ##SPC16## wherein R 1 is alkyl of 2-4 carbon atoms and R 2 is alkyl of 1-4 carbon atoms, with
Claim 5
Dependent Claim
43 words
b. an aqueous mineral acid at an elevated temperature for a period of time sufficient to form reaction products consisting essentially of a 2-(4-alkylphenyl)-propionaldehyde of the formula ##SPC17## and a 3-methyl-3-(4-alkylphenyl)-pyruvic acid of the formula ##SPC18## wherein R 1 has the above-indicated values.
Claim 6
Dependent Claim
43 words
b. an aqueous mineral acid at an elevated temperature for a period of time sufficient to form reaction products consisting essentially of a 2-(4-alkylphenyl)-propionaldehyde of the formula ##SPC17## and a 3-methyl-3-(4-alkylphenyl)-pyruvic acid of the formula ##SPC18## wherein R 1 has the above-indicated values.
Claim 7
Dependent Claim
16 words
A process according to claim 1, wherein the reaction is effected at a temperature of 80°-140°C.
Claim 8
Dependent Claim
16 words
A process according to claim 1, wherein said mineral acid is hydrochloric acid or sulfuric acid.
Claim 9
Dependent Claim
16 words
A process according to claim 1, wherein the reactants are dissolved in a lower aliphatic acid.
Claim 10
Dependent Claim
20 words
A process according to claim 4, wherein the reaction is effected at a temperatue of 80°-140°C. for about one hour.
Claim 11
Dependent Claim
38 words
A process according to claim 1, further comprising oxidizing at least one of said reaction products to form a 2-(4-alkylphenyl)-propionic acid of the formula ##SPC19## wherein R 1 has the above-indicated values, or a pharmaceutically acceptable salt thereof.
Claim 12
Dependent Claim
36 words
A process according to claim 6, wherein said propionaldehyde compound is oxidized with silver oxide under alkaline conditions in the presence of an alkali metal hydroxide to form an alkali metal salt of said propionic acid.
Claim 13
Dependent Claim
22 words
A process according to claim 6, wherein said propionaldehyde compound is oxidized with acidic aqueous potassium permanganate to form said propionic acid.
Claim 14
Dependent Claim
39 words
A process according to claim 6, wherein said pyruvic acid compound is oxidized with aqueous hydrogen peroxide under alkaline conditions in the presence of an alkali metal hydroxide to form an alkali metal salt of said propionic acid compound.
Claim 15
Dependent Claim
53 words
A process according to claim 6, wherein: a. the reaction is effected at a temperature of 80°-140°C. for about one hour to form said reaction products; and b. said propionaldehyde compound and said pyruvic acid compound are separated from each other and oxidized separately to form said propionic acid compound or salt thereof.
References Cited (Backward Citations)
US3435075A
Cited
GB1160725A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-06-22 | 1979-12-22 | 1980-06-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-06-22 | 1983-12-22 | 1984-06-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-06-22 | 1987-12-22 | 1988-06-22 | $7700.00 | Window Closed / Lapsed |