4-Aminophenol → 2-chloro-N-(4-hydroxyphenyl)acetamide

Participants

Reaction Steps

To a solution of 4-aminophenol (1.0 g, 9.1 mmol) in CH3COOH (3.5 mL) and saturated CH3COONa (3.5 mL), chloroacetylchloride (0.72 mL, 9.1 mmol) was added dropwise. After the addition was complete, the mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated, washed with water (3×25 mL) and dried over vacuum to isolate the intermediate 17a as white solid (0.690 g, 3.71 mmol, 40% yield). 1H NMR (DMSO, 400 MHz) δ 10.03 (s, 1H), 9.27 (s, 1H), 7.36 (d, J=8.8 Hz, 2H), 6.71 (d, J=8.8 Hz, 2H) 4.182 (s, 2H).

Provenance & Evidence