Methyl chloroacetate → (4-Nitrophenoxy)-acetic acid methoxycarbonylmethyl ester

Participants

Reaction Steps

To a mixture of (4-nitrophenoxy) acetic acid 22 (150 g, 761.4 mmol) and triethylamine (85 g, 840 mmol) in acetone (750 ml) was added methyl chloroacetate (91.6 g, 844 mmol) drop wise and stirred under reflux for 8 hours. Solids were filtered off and poured onto cold 5% sodium bicarbonate solution (4 L). Crude 44 was filtered, dried and recrystallised from chloroform:hexane (1:6) to get pure 44 (186 g, 90.8%) as a white powder with an m.p. between 88-90° C.

Provenance & Evidence