Ethanol → (2S)-3-(4-hydroxy-phenyl)-2-methoxypropionic acid ethyl ester

Participants

Reaction Steps

The compound of (2S)-3-(4-hydroxy-phenyl)-2-methoxy-propionic acid (5.1 mmol) was dissolved in 50 ml of ethanol and 0.3 ml (5.6 mmol) of sulfuric acid was added. The mixture was stirred at room temperature for 18 hours and then concentrated. The mixture was diluted with water (55 ml) and NaHCO3 was added (310 mg, 3.7 mmol). This mixture was extracted with ethyl acetate (4×20 mL), and the combined organic layers were dried (MgSO4) and then concentrated to produce a yellow oil. 1H-NMR (CDCl3, 200.15 MHz): 7.07 (d, 2H, J=8.6), 6.72 (d, 2H, J=8.6), 5.42 (br s, 1H), 4.18 (q, 2H, J=7.3), 3.92 (dd, 1H, J=6.7, 5.9), 3.36 (s, 3H), 2.95 (d, 2H, J=6.7), 1.23 (t, 3H, J=7.3).

Provenance & Evidence