2-Aminophenol → 2(3H)-Benzoxazolone

Participants

Reaction Steps

Triethylamine (27.0 mL) was added to a mixture of 2-aminophenol (10 g, 91.74 mmol) in CH2Cl2 (200 mL) at 5° C. A solution of bis(trichloromethyl) carbonate (9.35 g, 31.48 mmol) in dichloromethane (40 mL) was then added, maintaining the temperature below 10° C. The resulting solution was then maintained below 10° C. for 6 hours. The reaction mixture was then quenched by the addition of water (50 mL) and ethanol (20 mL). After 0.5 hours, the mixture was concentrated and then poured into 400 mL of H2O. After filtration, the filter cake was washed with hydrochloric acid (10%) and water to afford 10 g (48%) of benzo[d]oxazol-2(3H)-one as an off-white solid.

Provenance & Evidence