反应 #2271689

反应方程式

4-hydroxy-3-methylacetophenone

K2CO3

1.3-dibromopropane

→

1-[4-(3-bromopropoxy)-3-methylphenyl]ethanone

溶剂

acetonitrile

反应条件

后处理

1. 1
   温度was heated
2. 2
   温度at reflux for 6 hours
3. 3
   其他At the end of the reaction
4. 4
   其他the solvent was removed on a rotary evaporator
5. 5
   萃取the crude solid was extracted into dichloromethane (750 ml)
6. 6
   过滤The insolubles inorganics were filtered off
7. 7
   浓缩The dichloromethane solution was concentrated again to a crude oil (34.5 g)
8. 8
   其他Purification
9. 9
   洗涤eluted with 7:3 hexane
10. 10
    其他The material thus purified
11. 11
    其他was recrystallized from ethanol

实验过程

A mixture of 4-hydroxy-3-methylacetophenone (14.5 g, 96 mmol), K2CO3 (17.5 g, 144 mmol), and 1.3-dibromopropane (30 g, 144 mmol) in acetonitrile (400 ml) was heated at reflux for 6 hours. At the end of the reaction, the solvent was removed on a rotary evaporator, and the crude solid was extracted into dichloromethane (750 ml). The insolubles inorganics were filtered off. The dichloromethane solution was concentrated again to a crude oil (34.5 g). Purification was effected by flash chromatography over a silica gel column (SiO2, 150 g; eluted with 7:3 hexane:dichloromethane, 2 l; and then with dichloromethane 2 l). The material thus purified weighed 14.6 g (56%) and was recrystallized from ethanol gave analytically pure 1-[4-(3-bromopropoxy)-3-methylphenyl]ethanone, m.p.=59°-61° C. ANALYSIS: Calculated for C12H15BrO2: 53.15%C 5.58%H Found: 53.35%C 5.52%H

来源