تفاعل #83911

معادلة التفاعل

water

vanillin

K2CO3

1-bromo-3-chloropropane

→

4-(3-chloropropoxy)-3-methoxybenzaldehyde

المردود 37.0%

المذيبات

acetone

acetone

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةrefluxed for 0.5 hours
2. 2
   درجة الحرارةHeating
3. 3
   أخرىwas removed
4. 4
   workup.STIRRINGThe reaction was stirred
5. 5
   درجة الحرارةrefluxed for 16 hours
6. 6
   استخلاصThe aqueous mixture was extracted with diethyl ether
7. 7
   تجفيفthe extract was dried (MgSO4)
8. 8
   تركيزthe solution was concentrated
9. 9
   أخرىto afford an oil, which upon evacuation
10. 10
    أخرىchromatographed on silica gel with 50% ethyl acetatehexane as eluent

الإجراء التجريبي

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.

المصدر