Method for manufacturing 2-(hydroxymethyl) cyclopropane carboxylic acid compound

A technology of cyclopropane carboxylic acid and compound, which is applied in the field of preparation of 2-(hydroxymethyl) cyclopropane carboxylic acid compound, and can solve problems such as many steps and complex synthesis of raw materials

Inactive Publication Date: 2005-10-12
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But, as the preparation method of 2-(hydroxymethyl) cyclopropane carboxylic acid compound, the step of above-mentioned former method is many, and raw material is synthesized complicated; And latter method selectivity may not always meet the requirement, therefore remains to be developed industrially more favorable Preparation

Method used

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  • Method for manufacturing 2-(hydroxymethyl) cyclopropane carboxylic acid compound
  • Method for manufacturing 2-(hydroxymethyl) cyclopropane carboxylic acid compound
  • Method for manufacturing 2-(hydroxymethyl) cyclopropane carboxylic acid compound

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preparation example Construction

[0067] In the preparation method of the present invention, when using the mixture of the cis-isomer and the trans-isomer as the compound shown in the formula (1), the 2 shown in the formula (2) that keeps the ratio of the cis-isomer / trans-isomer can be obtained. -(hydroxymethyl)cyclopropanecarboxylic acid compound; and when using optically active body as the compound shown in formula (1), can obtain the 2-(hydroxymethyl) shown in the formula (2) that keeps its stereo configuration Optically active form of cyclopropanecarboxylic acid compound.

[0068] Therefore, as the obtained 2-(hydroxymethyl)cyclopropanecarboxylic acid compound represented by the formula (2), for example, 2-(hydroxymethyl)cyclopropanecarboxylic acid, 2-(hydroxymethyl)cyclopropanecarboxylic acid methyl Ester, ethyl 2-(hydroxymethyl)cyclopropanecarboxylate, tert-butyl 2-(hydroxymethyl)cyclopropanecarboxylate, cyclohexyl 2-(hydroxymethyl)cyclopropanecarboxylate, 2-(hydroxymethyl)cyclopropanecarboxylate Methyl...

Embodiment 1

[0075] Into a 200 mL Schlenk tube were added 2.6 g of ethyl 2-(benzyloxymethyl)-3,3-dimethylcyclopropanecarboxylate, 100 mL of 4.4% by weight formic acid / methanol solution, and 10% by weight of palladium / carbon 2.6 g, stirred at room temperature for 7 hours to react. Then, the reaction solution was filtered through diatomaceous earth to remove the catalyst, and then the obtained filtrate was concentrated to obtain ethyl 2-(hydroxymethyl)-3,3-dimethylcyclopropanecarboxylate in the form of a colorless transparent oil 1.7 g, yield 98%.

Embodiment 2

[0077] Under a nitrogen atmosphere, 193 g of a 23% aqueous sodium hydroxide solution was added to a 1 L four-necked flask, and heated to 110°C. To this aqueous solution, 222 g of a solution containing 48.9% of ethyl 2-(benzyloxymethyl)-3,3-dimethylcyclopropanecarboxylate was added dropwise over 3.5 hours. Hour. After cooling to room temperature, 333 ml of water and 111 ml of toluene were added for liquid separation to obtain an aqueous solution containing crude 2-(benzyloxymethyl)-3,3-dimethylcyclopropanecarboxylic acid sodium salt. Repeat the above liquid separation operation three times. 127 g of 35% hydrochloric acid and 111 ml of toluene were added to the obtained aqueous solution for liquid separation to obtain a toluene solution containing crude 2-(benzyloxymethyl)-3,3-dimethylcyclopropanecarboxylic acid. Repeat the above liquid separation operation three times. The obtained toluene solution was washed three times with 111 ml of water, and then concentrated to obtain ...

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Abstract

A process for production of 2-(hydroxymethyl)cyclo- propanecarboxylic acids represented by the general formula (2): (2) [wherein R<1> is hydrogen, linear, branched, or cyclic alkyl, or substituted or unsubstituted aryl; and R<2> and R<3> are each independently hydrogen or methyl], characterized by reacting a compound represented by the general formula (1): (1) [wherein R<1>, R<2>, and R<3> are each as defined above; and R<4> is C1-2 alkyl substituted with at least one member selected from among substituted aryl groups and unsubstituted aryl groups] with a hydrogen donor in the presence of a catalyst selected from the group consisting of ruthenium catalysts, cobalt catalysts, rhodium catalysts, nickel catalysts, palladium catalysts, and platinum catalysts.

Description

technical field [0001] The present invention relates to a method for producing 2-(hydroxymethyl)cyclopropanecarboxylic acid compound useful as an intermediate for producing formylcyclopropanecarboxylic acid compound used in the synthesis of chrysanthemic acid derivatives and the like. Background technique [0002] Tetrahedron: Asymmetry, 1995, 6, in scheme 2 of page 684, discloses the method for preparing methyl 2-(hydroxymethyl)cyclopropanecarboxylate from a compound prepared through multiple steps using glutamic acid as a starting material . In addition, in scheme 1 described in Tetrahedron, 2001, 57, page 6086, it is disclosed that the hydroxyl group of ethyl 2-(hydroxymethyl)-3,3-dimethylcyclopropanecarboxylate is acetylated, and the resulting diester A method for selective hydrolysis of compounds under alkaline conditions, etc. But, as the preparation method of 2-(hydroxymethyl) cyclopropane carboxylic acid compound, the step of above-mentioned former method is many, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/353C07C51/367C07C67/31
CPCC07C67/31C07C51/353C07C2101/02C07C51/367C07C2601/02C07C62/08C07C62/02C07C69/757
Inventor 南田龙板垣诚
Owner SUMITOMO CHEM CO LTD
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