Artemisia Ketone and Its Related Compounds from Alkenylmagnesium Halides and Carboxylic Acids

Abstract

Artemisia ketone and its related compounds were prepared from alkenylmagnesium chloride and lower carboxylic acids. By the reaction of 2, 2-dimethyl-3-butenoic acid and methallylmagnesium chloride, isoartemisia ketone was obtained in yield of 28%. Isomerization of isoartemisia ketone with p-toluenesulfonic acid gave artemisia ketone in yield of 84%. Similarly, 2, 5, 5, 8-tetramethyl-1, 7-nonadien-4-one was prepared from 2, 2, 5-trimethyl-4-hexenoic acid. (±) -ar-Turmerone was obtained from 3- (p-methylphenyl) butyric acid in the similar manner.