Studies on Chrysanthemic Acid

Part XII Racemization of Optically Active 2, 2-Dimethyl-3-(1′-oxo-2′-hydroxy-2′-methyl) propyl-1, 3-trans-cyclopropane-1-carboxylic Acid

Abstract

Methyl (-)-2, 2-dimethyl-3-(1′-oxo-2′-hydroxy-2′-methyl) propyl-1, 3-trans-cyclopropane-1-carboxylate was treated with potassium tert.-butylate and gave tert.-butyl ester of the racemic acid. Transesterification and simultaneous racemization of the two asymmetric carbon atoms on cyclopropane ring were observed.
From the racemic acid, (±)-trans-chrysanthemic acid was derived by means of Huang Minion modification using hydrazine hydrate and diethyleneglycol. Combination of these reactions makes it possible to derive racemic trans-chrysanthemic acid from optically active one.