Benzaldehyde → Ethyl phenylglycinate, D-

Reaktionsgleichung

[CH3:1][CH2:2][O:3][C:4]([CH:6]([NH2:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5].C(O)(=O)C(C(C(O)=O)O)O.C(=O)C1C=CC=CC=1>CO>[CH3:1][CH2:2][O:3][C:4]([C@H:6]([NH2:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5]

Komponenten

Versuchsvorschrift

A solution of ethyl DL-phenylglycinate (6.26 g., 35 mmole) and (+)-tartaric acid (5.56 g., 1.05 equiv.) in dry methanol containing benzaldehyde (7% v/v benzaldehyde, 1 equiv; total volume 46 ml.) at 50° was cooled from 50° to 22° and stirred for 25 hours. The solid was filtered off and washed with methanol containing 7% benzaldehyde (15 ml.) then methanol (10 ml.) and dried at 22°/2 mm. for 3 hours to give ethyl D-phenylglycinate (+)-hemitartrate as a mono-methanol solvate (5.50 g., 43%), m.p. 131°-135° [α]D24 - 48° (c 2.68, H2O).