P-Anisidine → N-(4-Methoxyphenyl)Acetamide

Participants

Reaction Steps

Acetic anhydride (16.0 mL, 169 mmol) was added dropwise over 1 h to a mixture of p-anisidine (20.0 g, 162 mmol) and dichloromethane (60 mL), with moderation by cooling in a water bath. The mixture was stirred at room temperature for 1 h, during which time a solid formed. Petroleum spirit (190 mL) was added, and the mixture was stirred for a further 1 h. The mixture was filtered and washed with petroleum spirit to afford 4-acetamidoanisole as a pale grey solid (25.8 g, 96%), m.p. 127-128° C. 1H NMR (399.7 MHz, CDCl3) δ 2.13, 3.78 (2 s, 2×3H, 2×CH3); 6.83 (app. d, 2H, J=8.8 Hz, BB′); 7.38 (app. d, 2H, J=8.8 Hz, AA′); 7.59 (br s, 1H, NH).

Provenance & Evidence