Hydrochloric Acid → Methyl 2-(4-aminophenoxy)propanoate

Participants

Reaction Steps

To a mixture of 2-(4-Amino-phenoxy)-propionic acid 63 (240 grams, 1.103 mmol), in Methanol (4.8 liters) was passed dry HCl gas at 10° C. for 1 hour and refluxed for 48 hours. Methanol (2.5 liter) was distilled, ice water (1 liter) was added and the pH was adjusted to 7.5 with K2CO3. Crude 64 was extracted into chloroform, washed with 5% NaHCO3 solution, water, dried over Na2SO4 and distilled to give 64 (80 grams, 37.2%) as a brown syrup. The structure was confirmed with NMR. IHNMR (CDCl3) δ 1.56 (d, 3H, CH3), 2.9 (bs, 2H, —NH2), 3.72 (s, 3H, ester), 4.58 (q, 1H, CH), 6.53 (d, 2H, Ar), 6.68 (d, 2H, Ar).

Provenance & Evidence