Methyl chloroacetate → HCID 3615705, compound

Participants

Reaction Steps

A mixture of 4-phenoxyaniline (30 g, 0.162 mol), methyl chloroacetate (21.3 ml, 0.243 mol) and sodium bicarbonate (27.2 g, 0.324 mol) was heated at 100°-120° C. with magnetic stirring for 24 hours. The resulting semi-solid was partitioned between dichloromethane (300 ml) and water (300 ml) then separated. The aqueous layer was extracted with dichloromethane (200 ml) and the organic extracts were combined. The extracts were washed with 2N hydrochloric acid (2×200 ml) and water (2×200 ml), dried (MgSO4) and evaporated to give a brown oil. This was heated with hexane (300 ml) to give an oil suspension. The hexane was decanted off and residual oil crystallised on cooling. The solid was triturated with ether/hexane 1:1 and filtered to give a brown solid (13.6 g, 33%) m.p. 80°-82° C. A second crop of a pale yellow solid was also given (10.5 g, 25%).

Provenance & Evidence