2-Nitroanisole → Methyl alpha-chloro-3-methoxy-4-nitrophenylacetate

Participants

Reaction Steps

A suspension of potassium t-butoxide (1.44 kg) in dimethylformamide(6.61) cooled to −5° C. to −10° C., was treated with a mixture of 2-nitroanisole (690 g) and methyl dichloroacetate (915 g) over 4 hours, whilst maintaining the temperature below −5° C. The reaction mixture was then treated with acetic acid (770 ml) and then with water (6.61) and then e extracted three times with tert-butyl methyl ether (5.51). The combined extracts were washed with water (5.51), then with saturated sodium bicarbonate solution (5.51), then with saturated brine (5.51) and then dried over magnesium sulphate to give a solution of methyl α-chloro-3-methoxy-4-nitrophenylacetate.

Provenance & Evidence