反应详情

温度

50 °C

4-Amino-2,6-dimethylanisole (4, 5 g, 33.2 mmol) was placed in a round-bottom flask fitted with a reflux condenser, and acetic anhydride (3.4 mL, 35.4 mmol) and acetic acid (3 mL, 53.1 mmol) were added sequentially. The mixture was heated to 50° C. for 4 h, cooled, poured into water and basified with saturated aq. sodium bicarbonate. The solution was extracted with methylene chloride, and the combined extracts were washed with brine and dried (MgSO4). Removing the solvent and recrystallizing the resulting solid from hexane-methylene chloride yielded 4-acetamido-2,6-dimethylanisole (7, 5.3 g, 83% yield). Spectral data: 1H NMR: δ 2.1 (s, 3H), 2.2 (s, 6H), 3.65 (s, 3H), 7.10 (s, 2H), 8.10 (s, 1H); 13C NMR: δ 16.1, 24.2, 60.0, 121.5, 131.8, 134.3, 154.3, 169.8; CI-HRMS: calcd. for C11H16NO2 (M+H+) 194.1181, fnd. 194.1181.

1. customfitted with a reflux condenser
2. temperaturecooled
3. extractionThe solution was extracted with methylene chloride
4. washthe combined extracts were washed with brine
5. dry with materialdried (MgSO4)
6. customRemoving the solvent
7. customrecrystallizing the resulting solid from hexane-methylene chloride