反応 #320079

反応方程式

4-hydroxybenzonitrile

NaOH

3-bromomethylheptane

→

4-(2-ethylhexyloxy)benzonitrile

収率 84.3%

溶媒

methylcellosolve

反応条件

後処理

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

実験手順

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.

出典