Process for prepn. of cyclopropane formic ether

A technology of cyclopropane formic acid and alkyl, which is applied in the field of preparing cyclopropane formic acid ester, and can solve problems such as ineffective industrial production methods

Inactive Publication Date: 2002-09-18
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, the methods using inorganic acids or organic acids having strong acidity cause conspicuous color due to side reactions, making these methods necessarily not effective as industrial production methods

Method used

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  • Process for prepn. of cyclopropane formic ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Add 0.43 gram of 2,2-dimethyl-3-(2-methyl-1-propenyl) cyclopropanecarboxylic acid (E / Z=80 / 20) in 10 milliliters test tube type reactor, 0.50 gram 3-benzene oxybenzyl alcohol, 5.8 mg of zirconium tetrachloride, and 5 mL of xylene. The reactor was equipped with a Dean-Stark trap and a condenser, and the reaction mixture was stirred at 145°C under reflux for 8 hours while separating and collecting the water produced in the reaction as a by-product in the trap . The reaction mixture thereof was analyzed by gas chromatography, and it was found that 2,2-dimethyl-3-(2-methyl- (3-phenoxyphenyl)methyl 1-propenyl)cyclopropanecarboxylate.

Embodiment 2

[0068] A reaction was carried out in a manner similar to that of Example 1, except that 9.4 mg of a complex of zirconium tetrachloride and 2-tetrahydrofuran was added instead of 5.8 mg of zirconium tetrachloride in Example 1.

[0069] The reaction mixture thereof was analyzed by gas chromatography, and it was found that 2,2-dimethyl-3-(2-methyl- (3-phenoxyphenyl)methyl 1-propenyl)cyclopropanecarboxylate.

Embodiment 3

[0071] The reaction was carried out in a similar manner to Example 1, except that 7.3 mg of zirconocene dichloride was added instead of 5.8 mg of zirconium tetrachloride in Example 1.

[0072] The reaction mixture thereof was analyzed by gas chromatography, and it was found that 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid was obtained in a yield of 97% (selectivity: 98%) based on alcohol species (3-phenoxyphenyl)methyl ester.

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Abstract

The invention discloses a method for preparing cyclopropane carboxylate of formula (1): the method comprises making cyclopropane carboxylate of formula (2) and formula ( 3) The monohydric compound reaction.

Description

field of invention [0001] The present invention relates to a process for the preparation of cyclopropane carboxylate. Background of the invention [0002] The preparation of carboxylic acid esters from carboxylic acids and alcohols using protic acid catalysts is known. A production method using sulfuric acid as a catalyst is disclosed (Japanese Patent Laid-Open No. 9-188649), and a method using p-toluenesulfonic acid as a catalyst is also disclosed (Japanese Patent Laid-Open No. 11-228491). [0003] However, the methods using inorganic acids or organic acids having strong acidity cause conspicuous color due to side reactions, making these methods necessarily not effective as industrial production methods. Summary of the invention [0004] According to the invention, cyclopropanecarboxylates can be conventionally prepared from cyclopropanecarboxylic acid and alcohols by dehydration reactions in the presence of the catalysts defined below. [0005] The invention provides a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/30C07C67/08C07D307/45
CPCC07C67/08C07D307/42C07C69/747C07C67/30
Inventor 惣田宏岩仓和宪
Owner SUMITOMO CHEM CO LTD
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