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>C(O)C>[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

Solutions of ethyl DL-phenylglycinate (5.0 g., 27.95 mmole), (+)-tartaric acid (4.417 g., 29.45 mmole, 1.05 equiv.), and benzaldehyde (2.85 ml., 27.95 mmole, 1.0 equiv.) in ethanol (total volume 47 ml.) were mixed at 58°. The solution was cooled to 20° to 26° and stirred for 24 hours to give a white solid which was washed with ethanol (2 × 10 ml.), and dried at 29°/2 mm. for 6 hours to give ethyl D-phenylglycinate (+)-hemitartrate as a mono-ethanol solvate (7.95 g., 76%), [α]D20 -47° (c 2.5, H2O).