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The preparation method of 5-[(4-chlorophenyl)methyl]-2,2-dimethylcyclopentanone

A technology of dimethylcyclopentanone and chlorophenyl is applied in the field of preparation of 5-[methyl]-2,2-dimethylcyclopentanone, and can solve the problems of low product yield, complicated operation and environmental pollution big problem

Active Publication Date: 2017-08-29
SHANGHAI HUAYI GRP CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The technical problem to be solved by the present invention is that the product yield in the prior art is low, the operation is complicated, and the problem of environmental pollution is relatively large, and a new 5-[(4-chlorophenyl)methyl]-2,2 -The preparation method of dimethylcyclopentanone

Method used

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  • The preparation method of 5-[(4-chlorophenyl)methyl]-2,2-dimethylcyclopentanone
  • The preparation method of 5-[(4-chlorophenyl)methyl]-2,2-dimethylcyclopentanone
  • The preparation method of 5-[(4-chlorophenyl)methyl]-2,2-dimethylcyclopentanone

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Embodiment 1

[0024] Add 80 g of methyl 1-[(4-chlorophenyl)methyl]-3,3-dimethyl-2-oxocyclopentanecarboxylate and 1,3-dimethylimidazole into a 1-liter three-necked flask 600ml of tetrafluoroborate was heated to 140°C and reacted for 8 hours. Cool the reacted solution to 100°C, distill under reduced pressure, collect the distillate at 130-135°C at a temperature of 165°C, and a pressure of 150 Pa to obtain 5-[(4-chlorophenyl)methyl]-2,2- Dimethylcyclopentanone 58g, yield 90.3%.

Embodiment 2

[0026] Add 60 g of 1-[(4-chlorophenyl)methyl]-3,3-dimethyl-2-oxocyclopentanecarboxylic acid methyl ester and 1-ethyl-3-methanol in a 1-liter three-necked flask 600ml of imidazole tetrafluoroborate was heated to 160°C and reacted for 5 hours. Cool the reacted solution to 100°C, distill under reduced pressure, collect the distillate at 130-135°C at a temperature of 165°C, and a pressure of 150 Pa to obtain 5-[(4-chlorophenyl)methyl]-2,2- Dimethylcyclopentanone 44g, yield 91.3%.

Embodiment 3

[0028] Add 80 g of ethyl 1-[(4-chlorophenyl)methyl]-3,3-dimethyl-2-oxocyclopentanecarboxylate and 1-butyl-3 chloride into a 1-liter three-necked flask -Methylimidazolium salt 600ml, heated to 160°C, reacted for 6 hours, cooled the reacted solution to 100°C, distilled under reduced pressure, the temperature was 155°C, and the pressure was 100Pa when collecting 120-130°C middle distillate to obtain 5-[ (4-Chlorophenyl)methyl]-2,2-dimethylcyclopentanone 57g, yield 92.9%.

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Abstract

The invention relates to a method for preparing 5-[(4-chlorophenyl)methyl]-2,2-dimethyl-cyclopentanone. The method is mainly used for solving the problems of lower product yield, complicated operation and larger environmental pollution in the prior art. The problems are well solved by adopting the following technical scheme that the method for preparing 5-[(4-chlorophenyl)methyl]-2,2-dimethyl-cyclopentanone comprises the following step of carrying out decarboxylation reaction on methyl 1-[(4-chlorophenyl)methyl]-3, 3-dimethyl-2-oxocyclopentanecarboxylate or ethyl 1-[(4-chlorophenyl)methyl]-3,3-dimethyl-2-oxo oxocyclopentanecarboxylate as a raw material in an ionic liquid at a reaction temperature of 100-180 DEG C to obtain 5-[(4-chlorophenyl)methyl]-2,2-dimethyl-cyclopentanone. The method can be used in preparation of 5-[(4-chlorophenyl)methyl]-2,2-dimethyl-cyclopentanone.

Description

technical field [0001] The invention relates to a preparation method of 5-[(4-chlorophenyl)methyl]-2,2-dimethylcyclopentanone. Background technique [0002] In the decarboxylation reaction of 1-[(4-chlorophenyl)methyl]-3,3-dimethyl-2-oxocyclopentanecarboxylate, the raw material is generally decarboxylated by hydrolysis under acidic or basic conditions . In "Journal of Natural Products" (1989,52(1),77-80), compounds of similar structure were heated to reflux in the presence of hydrochloric acid to obtain the target product; while in the patent CN1454200A, compounds of the same structure were found in Decarboxylation occurs under the conditions of acetic acid, water and sulfuric acid or decarboxylation reaction occurs in sodium hydroxide solution to obtain the target product. Subsequent treatment of such hydrolytic decarboxylation methods requires organic phase extraction to collect the target product. Since the acid-base solution cannot be reused and organic phase extracti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/697C07C45/65C07C45/67
CPCC07C45/676C07C2601/06C07C49/697
Inventor 龚磊袁振文王苏范曼曼廖本仁揭元萍
Owner SHANGHAI HUAYI GRP CO
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