반응 #83911

반응 방정식

water

vanillin

K2CO3

1-bromo-3-chloropropane

→

4-(3-chloropropoxy)-3-methoxybenzaldehyde

수율 37.0%

용매

acetone

acetone

반응 조건

후처리

1. 1
   온도refluxed for 0.5 hours
2. 2
   온도Heating
3. 3
   기타was removed
4. 4
   workup.STIRRINGThe reaction was stirred
5. 5
   온도refluxed for 16 hours
6. 6
   추출The aqueous mixture was extracted with diethyl ether
7. 7
   건조the extract was dried (MgSO4)
8. 8
   농축the solution was concentrated
9. 9
   기타to afford an oil, which upon evacuation
10. 10
    기타chromatographed on silica gel with 50% ethyl acetatehexane as eluent

실험 절차

A mixture of vanillin (30.4 g, 200 mmol), K2CO3 (27.6 g) and acetone (150 ml) was stirred and refluxed for 0.5 hours. Heating was removed and 1-bromo-3-chloropropane (40.8 g, 260 mmol) in acetone was added dropwise. The reaction was stirred and refluxed for 16 hours, and then it was poured into water. The aqueous mixture was extracted with diethyl ether, the extract was dried (MgSO4), and the solution was concentrated to afford an oil, which upon evacuation solidified to a white solid (50.2 g). An 8.0 g sample was flash chromatographed on silica gel with 50% ethyl acetatehexane as eluent. Concentration of appropriate fractions gave 2.7 g (37%) of 4-(3-chloropropoxy)-3-methoxybenzaldehyde as a white solid, m.p.=53°-55° C.

출처