Methanol → Phenylalanine, 4-chloro-, methyl ester

Participants

Reaction Conditions

Reaction Steps

4-Chloro-DL-phenylalanine (1.00 g, 5.00 mmol) was dissolved in methanol (30 mL) and cooled to 0° C. Thionyl chloride (2.92 mL, 40.0 mmol) was added dropwise. The mixture was allowed to warm to room temperature and was heated at reflux for 4 h. The solvent and reagents were removed in vacuo to yield the hydrochloride salt 1-1 as a white powder in quantitative yield (1.25 g, 5.00 mmol). 1H NMR (300 MHz, CD3OD): δ=7.37 (d, 2H, J=6.6 Hz), 7.27 (d, 2H, J=6.6 Hz), 4.34 (t, 1H, J=6.9 Hz), 3.81 (s, 3H), 3.26 (dd, 1H, J=14.4, 6.4 Hz), 3.18 (dd, 1H, J=14.4, 7.3 Hz); 13C NMR (75 mHz, CD3OD): δ=170.28, 134.87, 134.18, 132.11, 130.19, 54.99, 53.85, 38.81; ESI-MS calcd for C10H13ClNO2 [M+H]+: 214.0635. found 214.0638.

Provenance & Evidence