Hydrochloric Acid → 2-[4-(2-Hydroxycyclopentylidenemethyl)phenyl]propionic acid

Participants

Reaction Steps

123 mg of 2-[4-(2-oxocyclopentylidenemethyl)phenyl]propionic acid (which can be prepared as described in United Kingdom Patent Specification No. 2,002,762) and 75 mg of sodium cyanoborohydride were dissolved in 5 ml of methanol. The pH of the solution was adjusted to a value of 3 by the addition of 6N hydrochloric acid, whilst ice-cooling. The mixture was stirred under reflux for 40 minutes, after which it was diluted with ice-water and then extracted with diethyl ether. The extract was washed with water and then the solvent was distilled off to give crystals. These were recrystallised from a 1:1 by volume mixture of ethyl acetate and hexane, to give 80 mg of the title compound, melting at 125°-132° C.

Provenance & Evidence