Реакция #83911

Уравнение реакции

water

vanillin

K2CO3

1-bromo-3-chloropropane

→

4-(3-chloropropoxy)-3-methoxybenzaldehyde

Выход 37.0%

Растворители

acetone

acetone

Условия реакции

Обработка

1. 1
   Температураrefluxed for 0.5 hours
2. 2
   ТемператураHeating
3. 3
   Другоеwas removed
4. 4
   workup.STIRRINGThe reaction was stirred
5. 5
   Температураrefluxed for 16 hours
6. 6
   ЭкстракцияThe aqueous mixture was extracted with diethyl ether
7. 7
   Сушкаthe extract was dried (MgSO4)
8. 8
   Концентрированиеthe solution was concentrated
9. 9
   Другоеto afford an oil, which upon evacuation
10. 10
    Другоеchromatographed on silica gel with 50% ethyl acetatehexane as eluent

Методика

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.

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