反应详情

To a solution of 1-acetoxymethyl-3-nitro-2,4,6-trimethybenzene (6.0 g, 25.2 mmol) in methanol (100 mL) were sequentially added ammonium chloride (2.7 g in 25 mL of water), zinc powder (11 g). The exothermic reaction was vigorously stirred until it was back to RT (2 h). To work up the crude mixture was filtered off and the cake was washed with methanol. The methanolic solutions were concentrated to a volume of 20 mL, added 1 N HCl (300 mL). The insoluble material was removed by filtration, the solution was basified with solid NaHCO3. The semicrystalline precipitate was taken into ethyl acetate. The extract was concentrated and the residual product purified by means of column chromatography (25% ethyl acetate/hexane) to give 3-Acetoxymethyl-2,4,6-trimethylaniline as a pink oil (3.8 g, 75%).

1. customThe exothermic reaction
2. customwas back to RT
3. custom(2 h)
4. filtrationwas filtered off
5. washthe cake was washed with methanol
6. concentrationThe methanolic solutions were concentrated to a volume of 20 mL
7. additionadded 1 N HCl (300 mL)
8. customThe insoluble material was removed by filtration
9. concentrationThe extract was concentrated
10. customthe residual product purified by means of column chromatography (25% ethyl acetate/hexane)