Hydrochloric Acid → Benzyl (4-hydroxyphenyl)carbamate

Participants

Reaction Steps

10.1 g (0.12 mol) of sodium hydrogencarbonate and 17.2 ml (0.12 mol) of benzyloxycarbonyl chloride were added at 0° C. to a suspension of 12.5 g (0.11 mol) of p-aminophenol in 100 ml of a 1:1 by volume mixture of dioxane and water, and the mixture was stirred at room temperature for 18 hours. At the end of this time, the reaction mixture was acidified with 2N aqueous hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was triturated with a 1:1 by volume mixture of hexane and diethyl ether, to give 22.8 g of the title compound as colorless crystals, melting at 156°-157° C.

Provenance & Evidence