Hydrochloric Acid → Benzoyl-L-phenylalanine

Participants

Reaction Steps

To a mixture of phenylalanine (500 g, 3.03 mol), 2N aqueous sodium hydroxide solution (4 L) and ether (500 mL) was added dropwise benzoyl chloride (455 mL, 3.93 mol) under ice-cooling over about 55 min. The resulting mixture was stirred at room temperature for 16 h, cooled with ice and acidified with conc. hydrochloric acid to pH 2. The precipitated crystals were extracted with ethyl acetate. The obtained extracts were combined and washed with water, dried over anhydrous sodium sulfate and concentrated to ca. 2 L. Then hexane was added to the resulting suspension. The resulting precipitate was collected by filtration to give 815 g (100%) of N-benzoylphenylalanine.

Provenance & Evidence