تفاعل #160689

معادلة التفاعل

1,5-dibromopentane

vanillin

potassium carbonate

→

product 44

المردود 80.0%

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

المردود 80.0%

المذيبات

acetone

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was heated
2. 2
   درجة الحرارةat reflux for 2.5 hours
3. 3
   أخرىthe reaction
4. 4
   ترشيحThe suspension was subjected to vacuum filtration
5. 5
   أخرىthe resulting acetone solution was evaporated to dryness under reduced pressure
6. 6
   غسيلwashed with 10% ethyl acetate in hexane (2 L)
7. 7
   غسيلto elute
8. 8
   أخرىthe product, removal of excess solvent
9. 9
   أخرىby rotary evaporation under reduced pressure

الإجراء التجريبي

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).

المصدر