Patent JPS601874A successfully refreshed from Google Patents.
US4123451A
Expired / Lapsed
US
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Preparation of esters
Assignee: Shell USA Inc
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Filing: 1977-02-03
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Granted: 1978-10-31
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Expires: 1997-02-03
Abstract
Abstract Certain carboxylic acid esters also containing a cyano group are prepared by reacting an acid halide, an aldehyde and a water-soluble cyanide in the presence of one or more water-immiscible (cyclo)alkane solvents.
Inventors
- 👤 Roger A. Sheldon
- 👤 Peter Been
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 20:19
CPC Classifications
C; C07; C07C; C07C253/00; C07C253/14
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
117 words
A process for the preparation of an ester of formula I ##STR2## wherein Ar is a phenoxy substituted phenyl group and R is a branched-chain alkyl group substituted by a halophenyl group, which process comprises contacting an aromatic aldehyde of the formula ArC(O)H and an acyl halide of the formula RC(O)Hal, in which formulas Ar and R have the same meaning as in formula I and Hal represents a halogen atom having an atomic number of from 9 to 53, inclusive, with water and water-soluble cyanide in the presence of at least one substantially water-immiscible alkane solvent containing from 6 to 10 carbon atoms or mixture thereof and recovering the desired ester product from the reaction mixture.
Claim 2
Dependent Claim
117 words
A process for the preparation of an ester of formula I ##STR2## wherein Ar is a phenoxy substituted phenyl group and R is a branched-chain alkyl group substituted by a halophenyl group, which process comprises contacting an aromatic aldehyde of the formula ArC(O)H and an acyl halide of the formula RC(O)Hal, in which formulas Ar and R have the same meaning as in formula I and Hal represents a halogen atom having an atomic number of from 9 to 53, inclusive, with water and water-soluble cyanide in the presence of at least one substantially water-immiscible alkane solvent containing from 6 to 10 carbon atoms or mixture thereof and recovering the desired ester product from the reaction mixture.
Claim 3
Dependent Claim
12 words
A process according to claim 1, in which the alkane is n-heptane.
Claim 4
Dependent Claim
20 words
A process according to claim 1 in which the total amount of the water-soluble cyanide is dissolved in the water.
Claim 5
Dependent Claim
22 words
A process according to claim 1, which is conducted at a temperature in the range of from 10° C to 50° C.
Claim 6
Dependent Claim
14 words
A process according to claim 1, in which the water-soluble cyanide is sodium cyanide.
Claim 7
Dependent Claim
41 words
A process according to claim 1, in which the molar ratio of the amount of acyl halide of the formula RC(O)Hal to the amount of the aromatic aldehyde of the formula ArC(O)H is in the range of from 1.1 to 1.0.
Claim 8
Dependent Claim
24 words
A process according to claim 6, in which the molar ratio of the amount of acyl halide to the amount of aldehyde is 1.0.
Claim 9
Dependent Claim
17 words
A process according to claim 1, in which Hal in the formula RC(O)Hal represents a chlorine atom.
Claim 10
Dependent Claim
32 words
A process according to claim 1 in which the group R in the general formula RC(O)Hal is an alkyl group having a tertiary or quaternary carbon atom bound to the group --C(O)Hal.
Claim 11
Dependent Claim
15 words
A process according to claim 9, in which the group R is a 1-(4-chlorphenyl)-2-methylpropyl group.
Claim 12
Dependent Claim
40 words
A process according to claim 10, which is carried out by forming a mixture of the total amounts of the aromatic aldehyde, the acyl halide, the water, the water-soluble cyanide and the alkane, and stirring of the mixture thus formed.
Claim 13
Dependent Claim
63 words
A process according to claim 2 which is conducted at a temperature in the range of from 10° C to 50° C using sodium cyanide dissolved in water as the water-soluble cyanide and a molar ratio of acyl halide of the formula RC(O)Hal to the amount of the aromatic aldehyde of the formula ArC(O)H is in the range of from 1.1 to 1.0.
Claim 14
Dependent Claim
15 words
A process according to claim 12 wherein the ester of formula I is α-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutanoate.
References Cited (Backward Citations)
US3835176A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-10-30 | 1982-05-01 | 1982-10-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-10-30 | 1986-05-01 | 1986-10-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-10-30 | 1990-05-01 | 1990-10-31 | $7700.00 | Window Closed / Lapsed |