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US4061664A Expired / Lapsed US ⏱️ 0.0 years remaining

Preparation of phenoxybenzyl esters

Assignee: Shell USA Inc
•
Filing: 1976-11-01
•
Granted: 1977-12-06
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Expires: 1996-11-01
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Abstract

Abstract Phenoxybenzyl esters are prepared by neutralizing an aqueous solution of a carboxylic acid and contacting the neutralized solution with a solution of phenoxybenzyl halide in a water-immiscible base in the presence of a phase transfer catalyst.

Inventors

  • 👤 Derek A. Wood

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 07:02
CPC Classifications
C; C07; C07C; C07C255/00

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 261 words
A process for the preparation of a phenoxybenzyl ester of the formula ##STR5## wherein Q is a hydrogen atom or a cyano group and R is a. a cyclopropyl group of the formula ##STR6## in which R a and R b each is an alkyl group containing from 1 to 6 carbon atoms, or a halogen atom of atomic number from 9 to 35, inclusive, or R a is a hydrogen atom and R b is an alkenyl group containing from 2 to 6 carbon atoms optionally substituted by from 1 to b 3 chlorine or bromine atoms, R c R d each is an alkyl group containing from 1 to 6 carbon atoms, or R c is hydrogen and R d is R b , or R a and R b together or R c and R d together is an alkylene group containing from 2 to 6 carbon atoms; or b. a benzyl group of the formula ##STR7## in which Z is a halogen atom of atomic number 9 to 35, inclusive, or an alkoxy group containing from 1 to 4 carbon atoms and Y is an alkyl group containing from 1 to 6 carbon atoms, which process comprises neutralizing an acid of the formula R-COOH in which R is defined above with a water-soluble base, and then contacting the resulting product with a solution in a water-immiscible organic solvent of a benzyl halide of the formula ##STR8## in which X is a halogen atom; and Q is defined above in the presence of a macrocyclic polyether phase-transfer catalyst.
Claim 2
Dependent Claim 261 words
A process for the preparation of a phenoxybenzyl ester of the formula ##STR5## wherein Q is a hydrogen atom or a cyano group and R is a. a cyclopropyl group of the formula ##STR6## in which R a and R b each is an alkyl group containing from 1 to 6 carbon atoms, or a halogen atom of atomic number from 9 to 35, inclusive, or R a is a hydrogen atom and R b is an alkenyl group containing from 2 to 6 carbon atoms optionally substituted by from 1 to b 3 chlorine or bromine atoms, R c R d each is an alkyl group containing from 1 to 6 carbon atoms, or R c is hydrogen and R d is R b , or R a and R b together or R c and R d together is an alkylene group containing from 2 to 6 carbon atoms; or b. a benzyl group of the formula ##STR7## in which Z is a halogen atom of atomic number 9 to 35, inclusive, or an alkoxy group containing from 1 to 4 carbon atoms and Y is an alkyl group containing from 1 to 6 carbon atoms, which process comprises neutralizing an acid of the formula R-COOH in which R is defined above with a water-soluble base, and then contacting the resulting product with a solution in a water-immiscible organic solvent of a benzyl halide of the formula ##STR8## in which X is a halogen atom; and Q is defined above in the presence of a macrocyclic polyether phase-transfer catalyst.
Claim 3
Dependent Claim 14 words
A process according to claim 1 wherein X represents a chlorine or bromine atom.
Claim 4
Dependent Claim 14 words
A process according to claim 1 wherein the water-soluble base is an inorganic base.
Claim 5
Dependent Claim 24 words
A process according to claim 1 wherein the water-immiscible solvent is an organic liquid in which the benzyl halide is at least moderately soluble.
Claim 6
Dependent Claim 27 words
A process according to claim 1 wherein the phenoxybenzyl ester is an alpha-cyano-3-phenoxybenzyl ester of tetramethylcyclopropane carboxylic acid, dimethyl-dichlorovinyl-cyclopropane carboxylic acid, dimethyl-dibromovinyl-cyclopropane carboxylic acid, or 2-(4-chlorophenyl)-3-methylbutyric acid.

References Cited (Backward Citations)

GB912104A Cited
US3666789A Cited
US3931290A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-12-05 1981-06-06 1981-12-06 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-12-05 1985-06-06 1985-12-06 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-12-05 1989-06-06 1989-12-06 $7700.00 Window Closed / Lapsed

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