4-Aminophenol → Benzyl (4-hydroxyphenyl)carbamate

Participants

Reaction Steps

To a suspension of p-aminophenol (7.0 g, 63.9 mmol) in tetrahydrofuran (105 mL) was added saturated aqueous sodium hydrogen carbonate (70 mL), and benzyl chloroformate (12.0 g, 70.3 mmol) was added dropwise at 0° C. After stirring at room temperature for 16 hr, the reaction mixture was extracted with ethyl acetate (200 mL). The organic layer was washed with saturated brine (100 mL) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was washed with hexane/ethyl acetate (=4/1) and collected by filtration to give the title compound (8.2 g, 53%).

Provenance & Evidence