反应 #320079

反应方程式

4-hydroxybenzonitrile

NaOH

3-bromomethylheptane

→

4-(2-ethylhexyloxy)benzonitrile

收率 84.3%

溶剂

methylcellosolve

反应条件

后处理

1. 1
   其他equipped with stirrer
2. 2
   workup.WAITThe reaction is continued at 100° C. for about 12 hours
3. 3
   其他The solvent and excess bromide are removed in vacuo
4. 4
   萃取The resulting mixture is extracted three times with water
5. 5
   干燥the organic phase is dried over sodium sulfate
6. 6
   其他evaporated to dryness
7. 7
   workup.DISTILLATIONHigh-vacuum distillation through a 10-cm Vigreux column (127°-132° C., 0.15 mmHg)

实验过程

A 1 l sulfonating flask equipped with stirrer, cooler, dropping funnel and internal thermometer is charged with 61.4 g (0.5 mol) of 4-hydroxybenzonitrile in 500 ml of methylcellosolve. After heating the batch to 80° C., 73.3 g of 30% NaOH (0.55 mol) are slowly run in with vigorous stirring. Stirring is continued for 15 minutes before adding 116.8 g (0.575 mol) of 3-bromomethylheptane dropwise over a period of 30 minutes. The reaction is continued at 100° C. for about 12 hours. The thin-layer chromatogram shows almost quantitative conversion. The solvent and excess bromide are removed in vacuo, and the residue (oil) is taken up in 500 ml of toluene. The resulting mixture is extracted three times with water, the organic phase is dried over sodium sulfate and evaporated to dryness. High-vacuum distillation through a 10-cm Vigreux column (127°-132° C., 0.15 mmHg) gives 97.5 g (84% of theory) of 4-(2-ethylhexyloxy)benzonitrile as a coloured oil.

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