US4334079A
Expired / Lapsed
US
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Synthesis of substituted benzyl esters
Assignee: Eli Lilly and Co
•
Filing: 1980-11-03
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Granted: 1982-06-08
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Expires: 2000-11-03
Abstract
Abstract A process for preparing certain substituted benzyl esters of phenylacetic acids by esterification in a solvent in which the salt of the acid is insoluble, and in the presence of a phase transfer catalyst.
Inventors
- 👤 James M. Greene
- 👤 Charles A. Bunnell
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 12:16
CPC Classifications
C; C07; C07D; C07D505/00; C07D309/00; C07D309/02; C07D309/08; C07D309/10; C07D309/12
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
193 words
A process for preparing a compound of the formula ##STR5## wherein R 1 is hydroxy, protected hydroxy, hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halo; one of R 2 and R 3 is hydrogen and the other is phenoxy or C 1 -C 6 alkoxy; by reacting a compound of the formula ##STR6## with a compound of the formula ##STR7## wherein M is sodium or potassium, and X is chloro or bromo; in an organic solvent which is inert to esterification and in which the phenylacetic acid salt is substantially insoluble, and in the presence of a catalytic amount of a phase transfer catalyst of the formula X.sup.1 NR.sup.4 R.sup.5 R.sup.6 R.sup.7 wherein X 1 is chloro, bromo, iodo, toluenesulfonate or methanesulfonate; R 4 and R 5 are independently C 1 -C 16 alkyl, phenyl or benzyl; R 6 and R 7 are independently C 1 -C 16 alkyl; provided that, when X 1 is a group other than iodo, the process is carried out in the presence of from about 0.1 to about 0.5 mole of an alkali metal iodide per mole of product to be produced.
Claim 2
Dependent Claim
193 words
A process for preparing a compound of the formula ##STR5## wherein R 1 is hydroxy, protected hydroxy, hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halo; one of R 2 and R 3 is hydrogen and the other is phenoxy or C 1 -C 6 alkoxy; by reacting a compound of the formula ##STR6## with a compound of the formula ##STR7## wherein M is sodium or potassium, and X is chloro or bromo; in an organic solvent which is inert to esterification and in which the phenylacetic acid salt is substantially insoluble, and in the presence of a catalytic amount of a phase transfer catalyst of the formula X.sup.1 NR.sup.4 R.sup.5 R.sup.6 R.sup.7 wherein X 1 is chloro, bromo, iodo, toluenesulfonate or methanesulfonate; R 4 and R 5 are independently C 1 -C 16 alkyl, phenyl or benzyl; R 6 and R 7 are independently C 1 -C 16 alkyl; provided that, when X 1 is a group other than iodo, the process is carried out in the presence of from about 0.1 to about 0.5 mole of an alkali metal iodide per mole of product to be produced.
Claim 3
Dependent Claim
27 words
A process of claim 1 wherein the benzyl halide is a compound wherein one of R 2 and R 3 is hydrogen and the other is methoxy.
Claim 4
Dependent Claim
17 words
A process of claim 2 wherein the benzyl halide is a compound wherein R 2 is methoxy.
Claim 5
Dependent Claim
18 words
A process of claim 1 wherein the phenylacetic acid salt is a compound wherein R 1 is hydroxy.
Claim 6
Dependent Claim
18 words
A process of claim 3 wherein the phenylacetic acid salt is a compound wherein R 1 is hydroxy.
Claim 7
Dependent Claim
14 words
A process of claim 5 wherein the phenylacetic acid salt is a potassium salt.
Claim 8
Dependent Claim
13 words
A process of claim 6 wherein the benzyl halide is a benzyl chloride.
Claim 9
Dependent Claim
29 words
A process of any one of claims 1-7 wherein the phase transfer catalyst is a chloride or bromide, and the alkali metal iodide is a sodium or potassium iodide.
Claim 10
Dependent Claim
15 words
A process of any one of claims 1-7 wherein the organic solvent is a ketone.
Claim 11
Dependent Claim
11 words
A process of claim 9 wherein the organic solvent is acetone.
Claim 12
Dependent Claim
32 words
A process of any one of claims 1-7 wherein the amount of the phase transfer catalyst is from about 0.001 mole to about 0.1 mole per mole of product to be produced.
Claim 13
Dependent Claim
36 words
A process of any one of claims 1-7 wherein the phase transfer catalyst is a compound wherein each of R 4 , R 5 , R 6 and R 7 is C 1 -C 8 alkyl.
Claim 14
Dependent Claim
29 words
A process of claim 8 wherein the amount of the phase transfer catalyst is from about 0.001 mole to about 0.1 mole per mole of product to be produced.
Claim 15
Dependent Claim
12 words
A process of claim 13 wherein the organic solvent is a ketone.
Claim 16
Dependent Claim
11 words
A process of claim 14 wherein the organic solvent is acetone.
Claim 17
Dependent Claim
33 words
A process of claim 15 wherein the phase transfer catalyst is a compound wherein each of R 4 , R 5 , R 6 and R 7 is C 1 -C 8 alkyl.
Claim 18
Dependent Claim
13 words
A process of claim 11 wherein the phase transfer catalyst is an iodide.
Claim 19
Dependent Claim
11 words
A process of claim 17 wherein the solvent is a ketone.
Claim 20
Dependent Claim
33 words
A process of claim 18 wherein the phase transfer catalyst is a compound wherein each of R 4 , R 5 , R 6 and R 7 is C 1 -C 8 alkyl.
Claim 21
Dependent Claim
13 words
A process of claim 11 wherein the phase transfer catalyst is a toluenesulfonate.
Claim 22
Dependent Claim
11 words
A process of claim 20 wherein the solvent is a ketone.
Claim 23
Dependent Claim
33 words
A process of claim 21 wherein the phase transfer catalyst is a compound wherein each of R 4 , R 5 , R 6 and R 7 is C 1 -C 8 alkyl.
Claim 24
Dependent Claim
13 words
A process of claim 11 wherein the phase transfer catalyst is a methanesulfonate.
Claim 25
Dependent Claim
11 words
A process of claim 23 wherein the solvent is a ketone.
Claim 26
Dependent Claim
33 words
A process of claim 24 wherein the phase transfer catalyst is a compound wherein each of R 4 , R 5 , R 6 and R 7 is C 1 -C 8 alkyl.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-06-07 | 1985-12-07 | 1986-06-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-06-07 | 1989-12-07 | 1990-06-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-06-07 | 1993-12-07 | 1994-06-08 | $7700.00 | Window Closed / Lapsed |