反应 #740838

反应方程式

Isovanillin

Potassium carbonate

exo-2-bromonorbornane

→

green/brown oil

收率 87.2%

3-(Bicyclo[2.2.1]hept-2-yloxy)-4-Methoxybenzaldehyde

收率 87.2%

溶剂

water

反应条件

后处理

1. 1
   其他which is equipped with a stir bar
2. 2
   温度reflux condensor
3. 3
   workup.ADDITIONis charged with 500 ml of dimethylformamimde
4. 4
   温度the reaction mixture is heated to 120° C. for 48 hours
5. 5
   温度The reaction is then cooled to room temperature
6. 6
   萃取The aqueous layer is extracted with ethyl ether (3×100 ml)
7. 7
   洗涤The ethereal layer is washed with 1N sodium hydroxide solution (4×100 ml), water (3×100 ml) and saturated sodium chloride solution (3×100 ml)
8. 8
   干燥The organic layer is dried over anhydrous magnesium sulfate
9. 9
   过滤filtered
10. 10
    浓缩concentrated in vacuo

实验过程

Isovanillin (50 g, 0.328 mol) is placed in a 1 liter round bottom flask which is equipped with a stir bar and reflux condensor and is charged with 500 ml of dimethylformamimde. Potassium carbonate (45.3 g, 0.328 mol) is added to the reaction mixture which is heated to 80° C. At this temperature exo-2-bromonorbornane (12.57 g, 0.072 mol, 0.219 equivalents) is added and the reaction mixture is heated to 120° C. for 48 hours. The reaction is then cooled to room temperature and poured into 300 ml of water. The aqueous layer is extracted with ethyl ether (3×100 ml). The ethereal layer is washed with 1N sodium hydroxide solution (4×100 ml), water (3×100 ml) and saturated sodium chloride solution (3×100 ml). The organic layer is dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield 15.47 g of a green/brown oil. The crude product is purified by flash chromatography using a gradient eluent system of ethyl acetate/hexane [10% ethyl acetate/hexane→20% ethyl acetate/hexane] to yield 7.76 g (14.4%) of the aldehyde as a white solid. MP: 75.5° C.-79.5° C.

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