4-Aminophenol → Benzyl (4-hydroxyphenyl)carbamate

Participants

Reaction Steps

A solution of benzyl chloroformate (14 ml) in THF (30 ml) was added dropwise over 40 minutes to an ice-cold solution of 4-aminophenol (11 g) in THF (500 ml), the temperature of the reaction mixture being maintained at 0°-5° C. On completion of the addition, the reaction mixture was stirred at ambient temperature for 2 hours and the precipitated solid was collected and crystallised from a mixture of ethyl acetate and hexane to give 4-benzyloxycarbonylaminophenol (11.3 g) as a white solid: m.p. 153°-154° C.; Elemental Analysis: calculated for C14H13NO3 : C, 69.1%; H, 5.4%; N, 5.8%; found: C, 69.3%; H, 5.3%; N, 5.8%.

Provenance & Evidence