반응 #5665

반응 방정식

benzyl alcohol

benzyl 2,3,4,6-tetrafluorobenzoate

water

sodium hydride

→

6-benzyloxy-2,3,4-trifluorobenzoic acid

수율 31.6%

용매

n-hexane

acetic acid

acetic acid

benzene

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   기타reacted
3. 3
   기타followed by the removal of the solvent by distillation
4. 4
   workup.ADDITIONTo the residue, 6.5 g of potassium hydroxide and 50 ml of water and 100 ml of methanol were added
5. 5
   기타They were reacted at 50° C. for 30 minutes
6. 6
   기타followed by the removal of the solvent by distillation
7. 7
   workup.ADDITIONTo the residue were added 50 ml of benzene and 7% aq. potassium hydroxide solution
8. 8
   workup.STIRRINGThe resultant mixture was shaken
9. 9
   기타followed by separation into two layers
10. 10
    workup.ADDITIONConcentrated hydrochloric acid was added to the water layer so that the water layer
11. 11
    추출The thus-acidified water layer was extracted twice with 100 ml portions of chloroform
12. 12
    workup.ADDITIONThe extract was treated with anhydrous magnesium sulfate
13. 13
    workup.DISTILLATIONthe solvent was distilled out
14. 14
    기타A solid thus formed
15. 15
    여과collected by filtration

실험 절차

6.5 g of benzyl alcohol was dissolved in 150 ml of benzene. While the resultant solution was cooled with water, 2.4 g of sodium hydride (60%) was added and reacted. To the reaction mixture was added 15 g of benzyl 2,3,4,6-tetrafluorobenzoate, and stirred at room temperature for 1 hour. 3.6 g of acetic acid was added, followed by the removal of the solvent by distillation. To the residue, 6.5 g of potassium hydroxide and 50 ml of water and 100 ml of methanol were added. They were reacted at 50° C. for 30 minutes. 6 g of acetic acid was added, followed by the removal of the solvent by distillation. To the residue were added 50 ml of benzene and 7% aq. potassium hydroxide solution. The resultant mixture was shaken, followed by separation into two layers. Concentrated hydrochloric acid was added to the water layer so that the water layer was rendered acidic. The thus-acidified water layer was extracted twice with 100 ml portions of chloroform. The extract was treated with anhydrous magnesium sulfate and the solvent was distilled out. A solid thus formed was dispersed in n-hexane and then collected by filtration, whereby 4.7 g of 6-benzyloxy-2,3,4-trifluorobenzoic acid was obtained as colorless powder.

출처