Isobutanol → Isobutyl 2-(p-prenylphenyl)propionate

Participants

Reaction Conditions

Reaction Steps

To a solution of 21.8 g of 2-(p-prenylphenyl)propionic acid in 17.6 ml of pyridine and 200 ml of benzene was added dropwise a solution of 7.9 ml of thionyl chloride in 15 ml of benzene with stirring at 4° C. After one hour, 14.8 g of isobutyl alcohol was added. The mixture was stirred at room temperature for one hour and then at 60° C. for 2 hours. After cooling, the solution was washed with water, 2 N hydrochloric acid, water, 5% aqueous sodium hydroxide and water successively, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give 20.1 g of isobutyl 2-(p-prenylphenyl)propionate. b.p. 126°-127° C./0.10 mmHg, IR νmaxneat ; 1730 cm-1.

Provenance & Evidence