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

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Reaction Steps

To a mixture (4-Nitrophenoxy)acetic acid 94 (150 grams, 761.4 mmol), Triethylamine (85 grams, 840 mmol) in acetone (750 mL) was added methyl chloroacetate (91.6 grams, 844 mmol) drop wise, later stirred under reflux for 8 hours. Solids were filtered off and poured on to cold 5% sodium bicarbonate solution (4 lit). Crude 95 was filtered, dried, and recrystallized from chloroform:hexane (1:6) to get pure 95 (186 grams, 90.8%) as a white powder. M.p: 88-90° C. IH NMR (CDCl3) δ 3.80(s,3H,Ester), 4.75(s,2H,OCH2), 4.88(s,2H,OCH2), 7.02(d,2H,Ar), 8.22(d,2H,Ar).

Provenance & Evidence