Potassium Carbonate → 2-Acetylamino-4-nitrophenyl beta-hydroxypropyl ether

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Reaction Steps

0.5 mol (117 g) of the potassium salt of 4-nitro-2-acetylaminophenol is introduced into 300 ml of dimethylformamide in a boiling water-bath, with stirring. The mixture is treated with 0.5 mol (47.25 g) of 1-chloropropan-2-ol. With the heating maintained, 0.5 mol (47.25 g) of 1-chloropropan-2-ol and 0.25 mol (34.5 g) of potassium carbonate are added four times at 2-hour intervals. After heating for 10 hours, the reaction mixture is poured into 1,500 ml of iced water. The expected product, which has precipitated, is filtered off. It is washed with a 0.5N solution of sodium hydroxide and then with water. After drying in vacuo at 60° C., it melts at 123° C.

Provenance & Evidence