L-Phenylalanine → 3-Phenyllactic acid, (S)-

Participants

Reaction Conditions

Reaction Steps

A solution of sodium nitrite (51.8 g, 720 mmol) in 200 mL of water was added dropwise over 6 hours to a stirred solution of L-phenylalanine (33.04 g, 200 mmol) in 500 mL of 10% sulfuric acid at 50° C. After the addition was complete, the reaction mixture was stirred for 3 hours at 50° C, then at room temperature overnight. The reaction mixture was extracted with ethyl acetate (3×200 mL, 2×100 mL), then the combined organic extract was washed with water and brine, dried over sodium sulfate and evaporated to yield 28.98 g of a yellow solid. Recrystallization from benzene afforded 22.15 g of the title A compound as white needles, m.p. 120°-124° C.

Provenance & Evidence