Method of epimerization of alkyl chrysanthemate

Details Method of epimerization of alkyl chrysanthemate Method of epimerization of alkyl chrysanthemate

1982-03-18

1984-09-25

Shippen, Michael L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

562506, C07C 67333

Patent

active

044737033

ABSTRACT:
A process for isomerization of cis-chrysanthemate esters by contacting a chrysanthemate ester containing a cis-chrysanthemate ester with a Lewis acid, to transform the cis-chrysanthemate ester into trans-chrysanthemate ester through epimerization at C.sub.3 -position. The starting cis-chrysanthemate ester may be of any optical isomer ratio form (+)-form to (-)-form, including racemic form. Accordingly the process is effectively employable for the preparation of a (+)-trans-chrysanthemate ester from the (+)-cis-chrysanthemate ester. Combinations of the process with optical resolution would make the commercial production of (+)-trans-chrysanthemic acid more effective, the latter being an important acid component of pyrethroidal insecticides.

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Williams et al., Tetrahedron Letters, vol. 22, pp. 385-388 (1981).
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