Hydrochloric Acid → 3-{4-[(3,4-Difluorophenyl)methoxy]phenyl}prop-2-enoic acid

Participants

Reaction Conditions

Reaction Steps

2.5 g (15.2 mmol) p-cumaric acid is dissolved 100 ml ethyl methyl ketone. 4.21 g (30.5 mmol) potassium carbonate and 6.31 g (30.5 mmol) 3,4-difluorobenzyl bromide are added and the reaction mixture is hold at 70° C. over night. Dilution with water and extraction with ethyl acetate leaves a solid which is recrystallised from diethyl ether/n-hexane. The crude ester so obtained is dissolved in 100 ml THF and treated with 30.5 ml (30.5 mmol) of an aqueous 1 N sodium hydroxide solution. The mixture is heated to 50° C. for 6 hours, cooled and acidified with 1 N hydrochloric acid. The precipitate is filtered off and dried to yield 3.24 g (73%) of a colorless solid. MS: m/e=288.9 (M−H).

Provenance & Evidence