US4415751A
Expired / Lapsed
US
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Process for preparing phenylalkanoic acids
Assignee: Eli Lilly and Co
•
Filing: 1982-03-24
•
Granted: 1983-11-15
•
Expires: 2002-03-24
Abstract
Abstract Hydroxyphenylacetic acids are formed from the corresponding benzaldehydes or alkyl phenyl ketones by reduction, cyanation and hydrolysis without isolation or purification of intermediate products.
Inventors
- 👤 James M. Greene
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 10:12
CPC Classifications
C; C07; C07C; C07C51/00; C07C51/08; C07D; C07D263/00; C07D263/52; C07D263/54; C07D263/56; C07D263/57
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
195 words
A process for preparing an acid of the formula ##STR5## wherein R is hydrogen or C 1 -C 3 alkyl; one of R 1 and R 2 is hydrogen and the other is hydroxy; provided that R is hydrogen or methyl when R 2 is hydroxy; comprising catalytically hydrogenating a compound of the formula ##STR6## in the presence of an inert organic solvent, and optionally in the presence of an amine of the formula HNR.sup.3 R.sup.4 wherein R 3 is C 1 -C 3 alkyl and R 4 is hydrogen or C 1 -C 3 alkyl, to prepare a compound of the formula ##STR7## wherein R 5 is --NR 3 R 4 if an amine is present, and is --OH if an amine is not present; adding an alkali metal cyanide to the mixture; holding the mixture at from about 100° to about 150° until a compound of the formula ##STR8## is formed; removing the solvent; adding aqueous alkali metal hydroxide; holding the mixture at about 75°-125° until the product is formed; making the mixture acid; cooling the mixture; extracting the mixture with an inert organic solvent; and isolating the acid from the organic solvent.
Claim 2
Dependent Claim
195 words
A process for preparing an acid of the formula ##STR5## wherein R is hydrogen or C 1 -C 3 alkyl; one of R 1 and R 2 is hydrogen and the other is hydroxy; provided that R is hydrogen or methyl when R 2 is hydroxy; comprising catalytically hydrogenating a compound of the formula ##STR6## in the presence of an inert organic solvent, and optionally in the presence of an amine of the formula HNR.sup.3 R.sup.4 wherein R 3 is C 1 -C 3 alkyl and R 4 is hydrogen or C 1 -C 3 alkyl, to prepare a compound of the formula ##STR7## wherein R 5 is --NR 3 R 4 if an amine is present, and is --OH if an amine is not present; adding an alkali metal cyanide to the mixture; holding the mixture at from about 100° to about 150° until a compound of the formula ##STR8## is formed; removing the solvent; adding aqueous alkali metal hydroxide; holding the mixture at about 75°-125° until the product is formed; making the mixture acid; cooling the mixture; extracting the mixture with an inert organic solvent; and isolating the acid from the organic solvent.
Claim 3
Dependent Claim
10 words
A process of claim 1 wherein an amine is used.
Claim 4
Dependent Claim
14 words
A process of claim 2 for preparing an acid wherein R 1 is hydroxy.
Claim 5
Dependent Claim
13 words
A process of claim 3 for preparing an acid wherein R is hydrogen.
Claim 6
Dependent Claim
13 words
A process of claim 3 for preparing an acid wherein R is methyl.
Claim 7
Dependent Claim
13 words
A process of either claim 2 or 5 wherein the amine is methylamine.
Claim 8
Dependent Claim
13 words
A process of either claim 2 or 4 wherein the amine is dimethylamine.
Claim 9
Dependent Claim
10 words
A process of claim 2 wherein the amine is methylamine.
Claim 10
Dependent Claim
10 words
A process of claim 2 wherein the amine is dimethylamine.
Claim 11
Dependent Claim
17 words
A process of any one of claims 2-5 or 8-9 wherein the inert organic solvent is dimethylformamide.
Claim 12
Dependent Claim
18 words
A process of any one of claims 2-5 or 8-9 wherein the alkali metal cyanide is sodium cyanide.
Claim 13
Dependent Claim
18 words
A process of any one of claims 2-5 or 8-9 wherein the alkali metal hydroxide is sodium hydroxide.
Claim 14
Dependent Claim
29 words
A process of any one of claims 2-5 or 8-9 wherein the mixture is held at about the reflux temperature after the addition of the aqueous alkali metal hydroxide.
Claim 15
Dependent Claim
26 words
A process of any one of claims 2-5 or 8-9 wherein the extraction is with an inert organic solvent which is an ester or an ether.
Claim 16
Dependent Claim
13 words
A process of claim 10 wherein the alkali metal cyanide is sodium cyanide.
Claim 17
Dependent Claim
13 words
A process of claim 15 wherein the alkali metal hydroxide is sodium hydroxide.
Claim 18
Dependent Claim
23 words
A process of claim 16 wherein the mixture is held at about the reflux temperature after the addition of the aqueous sodium hydroxide.
Claim 19
Dependent Claim
21 words
A process of claim 17 wherein the extraction is with an inert organic solvent which is an ester or an ether.
Claim 20
Dependent Claim
10 words
A process of claim 18 wherein the amine is dimethylamine.
Claim 21
Dependent Claim
10 words
A process of claim 18 wherein the amine is methylamine.
Claim 22
Dependent Claim
10 words
A process of claim 1 wherein no amine is used.
Claim 23
Dependent Claim
14 words
A process of claim 21 for preparing an acid wherein R 1 is hydroxy.
Claim 24
Dependent Claim
13 words
A process of claim 22 for preparing an acid wherein R is hydrogen.
Claim 25
Dependent Claim
13 words
A process of claim 22 for preparing an acid wherein R is methyl.
Claim 26
Dependent Claim
15 words
A process of any one of claims 21-24 wherein the inert organic solvent is dimethylformamide.
Claim 27
Dependent Claim
16 words
A process of any one of claims 21-24 wherein the alkali metal cyanide is sodium cyanide.
Claim 28
Dependent Claim
16 words
A process of any one of claims 21-24 wherein the alkali metal hydroxide is sodium hydroxide.
Claim 29
Dependent Claim
27 words
A process of any one of claims 21-24 wherein the mixture is held at about the reflux temperature after the addition of the aqueous alkali metal hydroxide.
Claim 30
Dependent Claim
24 words
A process of any one of claims 21-24 wherein the extraction is with an inert organic solvent which is an ester or an ether.
Claim 31
Dependent Claim
13 words
A process of claim 25 wherein the alkali metal cyanide is sodium cyanide.
Claim 32
Dependent Claim
13 words
A process of claim 30 wherein the alkali metal hydroxide is sodium hydroxide.
Claim 33
Dependent Claim
23 words
A process of claim 31 wherein the mixture is held at about the reflux temperature after the addition of the aqueous sodium hydroxide.
Claim 34
Dependent Claim
21 words
A process of claim 32 wherein the extraction is with an inert organic solvent which is an ester or an ether.
Claim 35
Dependent Claim
26 words
A process of claim 26 wherein the solvent in the reduction step is methanol, which solvent is removed after the reduction step and replaced with dimethylformamide.
Claim 36
Dependent Claim
13 words
A process of claim 34 wherein the alkali metal hydroxide is sodium hydroxide.
Claim 37
Dependent Claim
23 words
A process of claim 35 wherein the mixture is held at about the reflux temperature after the addition of the aqueous sodium hydroxide.
Claim 38
Dependent Claim
21 words
A process of claim 36 wherein the extraction is with an inert organic solvent which is an ester or an ether.
References Cited (Backward Citations)
USRE29608E
Cited
US3984460A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-11-14 | 1987-05-16 | 1987-11-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-11-14 | 1991-05-16 | 1991-11-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-11-14 | 1995-05-16 | 1995-11-15 | $7700.00 | Window Closed / Lapsed |