반응 #160689

반응 방정식

1,5-dibromopentane

vanillin

potassium carbonate

→

product 44

수율 80.0%

4-(6-bromo-hexanoyl)-3-methoxy-benzaldehyde

수율 80.0%

용매

acetone

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도at reflux for 2.5 hours
3. 3
   기타the reaction
4. 4
   여과The suspension was subjected to vacuum filtration
5. 5
   기타the resulting acetone solution was evaporated to dryness under reduced pressure
6. 6
   세척washed with 10% ethyl acetate in hexane (2 L)
7. 7
   세척to elute
8. 8
   기타the product, removal of excess solvent
9. 9
   기타by rotary evaporation under reduced pressure

실험 절차

An excess of 1,5-dibromopentane (100 g, 3 equivalents) was added to a suspension of vanillin (43) (22 g) and potassium carbonate (30 g) in acetone (700 mL). The reaction mixture was heated at reflux for 2.5 hours and then allowed to stir at room temperature overnight, at which time TLC and LC/MS showed the reaction to be complete. The suspension was subjected to vacuum filtration and the resulting acetone solution was evaporated to dryness under reduced pressure. The residue was applied to a pad of silica gel and washed with 10% ethyl acetate in hexane (2 L) followed by 25% ethyl acetate in hexane to elute the product, removal of excess solvent by rotary evaporation under reduced pressure afforded the product 44 as an oil which crystallised on standing in freezer (35 g, 80% yield).

출처