4-Cyanophenol → 4-(2-Ethylhexyloxy)benzonitrile

HRID 232897

反応式

HRID 232897 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:13][CH:14]([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:15][CH3:16]>COCCO>[CH2:15]([CH:14]([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[CH3:16]

参加物

5

反応物 3

HCID 130194-CyanophenolHCID 14798Sodium HydroxideHCID 868042-Ethylhexyl bromide

生成物 1

HCID 190861874-(2-Ethylhexyloxy)benzonitrile収率 84.3%

試薬・触媒・溶媒 1

HCID 80192-Methoxyethanol溶媒

反応条件

温度
80 °C

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.

後処理

  1. customequipped with stirrer
  2. waitThe reaction is continued at 100° C. for about 12 hours
  3. customThe solvent and excess bromide are removed in vacuo
  4. extractionThe resulting mixture is extracted three times with water
  5. dry with materialthe organic phase is dried over sodium sulfate
  6. customevaporated to dryness
  7. distillationHigh-vacuum distillation through a 10-cm Vigreux column (127°-132° C., 0.15 mmHg)

出典と根拠

ORDレコード
ord-3387aa3b59354250b01117f6086baaa2
出典データセット
uspto-grants-1997_01
特許番号
US05591850

関連ノート

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