反应详情

Sodium bicarbonate (51 g, 0.607 mol) was suspended in 1,2-dimethoxyethane (180 ml), and methyl(3-amino-4-hydroxyphenyl)acetate (58.26 g, 0.32 mol) was added, followed by a further quantity of 1,2-dimethoxyethane (75 ml). To this mixture was added, dropwise, a solution of heptafluorobutyryl chloride (112.5 g, 0.48 mol) in 1,2-dimethoxyethane (140 ml), at such a rate that the reaction temperature was maintained at 19-20° C. Once the addition was complete, the mixture was stirred at room temperature for 1½ hours. The reaction mixture was filtered and the solid was taken up in ethyl acetate and washed with saturated aqueous bicarbonate solution and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was taken up in acetone (450 ml) and water (450 ml) was added. The mixture was stirred for 1½ hours, during which time an oil separated. The aqueous acetone was decanted and a further quantity (250 ml) of water was added to the oil. The mixture was stirred for 1 hour, during which time the desired product crystallised; it was collected by filtration, washed with water and dried to give methyl(3-heptafluorobutyramido-4-hydroxyphenyl)acetate (87.0 g).

1. additionTo this mixture was added
2. additionOnce the addition
3. filtrationThe reaction mixture was filtered
4. washwashed with saturated aqueous bicarbonate solution and brine
5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
6. filtrationfiltered
7. customthe filtrate was evaporated in vacuo
8. additionwater (450 ml) was added
9. stirringThe mixture was stirred for 1½ hours, during which time an oil
10. customseparated
11. customThe aqueous acetone was decanted
12. additiona further quantity (250 ml) of water was added to the oil
13. stirringThe mixture was stirred for 1 hour, during which time the desired product
14. customcrystallised
15. filtrationit was collected by filtration
16. washwashed with water
17. customdried