Hydrochloric Acid → Ethyl 4-(2'-fluoro-4-biphenylyl)-4-oxo-butyrate

Participants

Reaction Conditions

Reaction Steps

26.6 gm (0.2 mol) of powdered aluminum chloride were introduced over a period of 15 minutes into a mixture consisting of 17.2 gm (0.1 mol) of 2-fluoro-biphenyl, 16.4 gm (0.1 mol) of ethyl succinate chloride and 200 ml of ethylene chloride at 10° C, accompanied by stirring, and the resulting mixture was heated for 3 hours at 60° C. Thereafter, the reaction mixture was allowed to stand for several hours at room temperature, was then poured into a mixture of ice and hydrochloric acid, and 200 ml of ether were added to the mixture. The organic phase was separated, washed with water, with aqueous sodium bicarbonate and again with water, dried over sodium sulfate, and the solvent was distilled off. The oily residue was distilled in vacuo, yielding 23.1 gm (77% of theory) of ethyl 4-(2'-fluoro-4-biphenylyl)-4-oxo-butyrate, b.p. 190°-192° C at 0.4 mm Hg, which solidified into a crystalline substance after standing for some time and had a melting point of 56°-58° C after recrystallization from petroleum ether.

Provenance & Evidence