Hydrochloric Acid → 2-[4-(2-Hydroxyiminocyclopentan-1-ylmethyl)phenyl]propionic Acid

Participants

Reaction Steps

To a solution of 1.5 g of 2-[4-(2-oxocyclopentan-1-ylmethyl)phenyl]propionic acid in 10 ml of ethanol was added a solution of 0.43 g of hydroxylamine hydrochloride in 2 ml of water, subsequently a solution of 0.76 g of sodium hydroxide in 2 ml of water, and the mixture was heated under reflux for 3 hours. The reaction mixture was poured into an ice-water, acidified by addition of hydrochloric acid, and then extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and the solvent removed by distillation to give 1.4 g of crystals of the desired compound. Recrystallization of the product from a mixture of ether-n-hexane afforded colorless crystals, m.p. 146°-148° C.

Provenance & Evidence