Acetone → (R)-Amino-phenyl-acetic acid ethyl ester

Participants

Reaction Steps

A solution of ethyl DL-phenylglycinate (5.00 g., 28 mmole) and (+)-tartaric acid (4.18 g., 28 mmole, 1 equiv.) in ethanol (50 ml.) was made at 58°. The solution was cooled, acetone (4.1 ml., 55.6 mmole, 2 equiv.) was added and the mixture was stirred at 20° to 25° for 165 hours. The solid was filtered off, washed with ethanol (2 × 10 ml.) and dried at 26°/2 mm. for 41/2 hours to give ethyl D-phenylglycinate (+)-hemitartrate as a monoethanol solvate (9.338 g., 89%), [α]D -46.5° (c 2.5 H2O).

Provenance & Evidence