Methyl iodide → Methyl 2-(3-benzoylphenyl)propanoate

Participants

Reaction Steps

138 ml of a solution of 1.55N butyl lithium in hexane was introduced over 20 minutes at -40° C to a mixture of 775 ml of tetrahydrofuran, 775 ml of hexamethyl phosphor-triamide and 21.5 ml of diethylamine and after stirring for 20 minutes, a solution of 52.5 g of the above ester in 470 ml of tetrahydrofuran was added over 20 minutes. Then, 38 ml of methyl iodide were added thereto and the mixture was stirred for 30 minutes at about -40° C and then was progressively returned to 20° C. The reaction mixture was poured into 3 liters of water-ice mixture and was stirred and extracted with isopropyl ether. The extracts were washed with water and evaporated to dryness under reduced pressure to obtain methyl 2-(m-benzoyl-phenyl)-propionate which was used as is for the saponification.

Provenance & Evidence