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

Participants

Reaction Steps

A mixture of ethyl DL-phenylglycinate (5.021 g., 96% pure i.e. 27.0 mmole) and (+)-tartaric acid (2.027 g., 13.5 mmole, 0.5 equiv.) in ethanol (47 ml.) and benzaldehyde (2.75 ml., 2.88 g., 27.1 mmole, 1 equiv.) was stirred at 20°; crystallisation began within 5 minutes. After 10 days the mixture was filtered and the product washed with ethanol (2 × 7 ml.) and dried at 20°/4 mm. for 3 hours giving ethyl D-phenylglycinate (+)-hemitartrate solvated with 1.0 mole ethanol (3.922 g., 39% yield based on ester present or 78 % yield based on (+)-tartaric acid present), [α]D21 - 45.9° (c 2.506, H2O).

Provenance & Evidence