반응 #76440

반응 방정식

heptafluorobutyryl chloride

Sodium bicarbonate

methyl(3-amino-4-hydroxyphenyl)acetate

→

methyl(3-heptafluorobutyramido-4-hydroxyphenyl)acetate

수율 72.1%

용매

1,2-dimethoxyethane

1,2-dimethoxyethane

1,2-dimethoxyethane

반응 조건

후처리

1. 1
   workup.ADDITIONTo this mixture was added
2. 2
   workup.ADDITIONOnce the addition
3. 3
   여과The reaction mixture was filtered
4. 4
   세척washed with saturated aqueous bicarbonate solution and brine
5. 5
   건조The organic phase was dried over anhydrous magnesium sulfate
6. 6
   여과filtered
7. 7
   기타the filtrate was evaporated in vacuo
8. 8
   workup.ADDITIONwater (450 ml) was added
9. 9
   workup.STIRRINGThe mixture was stirred for 1½ hours, during which time an oil
10. 10
    기타separated
11. 11
    기타The aqueous acetone was decanted
12. 12
    workup.ADDITIONa further quantity (250 ml) of water was added to the oil
13. 13
    workup.STIRRINGThe mixture was stirred for 1 hour, during which time the desired product
14. 14
    기타crystallised
15. 15
    여과it was collected by filtration
16. 16
    세척washed with water
17. 17
    기타dried

실험 절차

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).

출처