Diethyl Sulfate → Ethyl alpha-[p-(3-methyl-2-butenyl)phenyl]propionate

Participants

Reaction Steps

A mixture of 20.0 g of 2-(p-prenylphenyl)propionic acid and 14.0 g of potassium carbonate in 150 ml of acetone was stirred at room temperature for one hour. To the solution was added dropwise a solution of 15.6 g of diethyl sulfate in 50 ml of acetone with stirring at 25° C. After stirring at room temperature for 3 hours, the mixture was refluxed for an additional one hour with stirring. The precipitate which formed was removed by filtration, and the acetone was evaporated. To the residue was added ice-water, and the mixture was extracted with n-hexane. The extract was washed with water, aqueous sodium bicarbonate and brine successively, and dried over anhydrous magnesium sulfate. The solvent was evaporated to give 18.7 g of ethyl 2-(p-prenylphenyl)propionate. b.p. 108° C./0.15 mmHg, IR νmaxneat ; 1730 cm-1.

Provenance & Evidence