反应详情

温度

70 °C

4-Nitrophenol (13.9 g, 100 mmol) was dissolved in N,N-dimethylformamide (20 ml), and t-butyl bromoacetate (29.3 g, 150 mmol) and potassium carbonate (27.6 g, 200 mmol) were added, which was followed by stirring at 70° C. for 4 hours. The reaction mixture was diluted with ethyl acetate (100 ml), washed with water, and the aqueous layer was extracted with ethyl acetate. The extract and the previously-obtained organic layer were combined. The mixture was washed with water and dried over anhydrous magnesium sulfate. After filtration, low boiling matters were distilled away from the filtrate under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1) and recrystallized from a mixed solvent of ethyl acetate and n-hexane to give 21.8 g of t-butyl 4-nitrophenoxyacetate as pale-yellow crystals (86%).

1. washwashed with water
2. extractionthe aqueous layer was extracted with ethyl acetate
3. extractionThe extract
4. washThe mixture was washed with water
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationAfter filtration, low boiling matters
7. distillationwere distilled away from the filtrate under reduced pressure
8. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1)
9. customrecrystallized from a mixed solvent of ethyl acetate and n-hexane