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

HRID 2294672

反応式

HRID 2294672 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

実験手順

61.4 g (0.5 mol) of 4-hydroxybenzonitrile in 500 ml of methylcellosolve are placed in a 1 l sulfonating flask fitted with stirrer, condenser, dropping funnel and internal thermometer. The batch is heated to 80 C., and then 73.3 g of 30% NaOH (0.55 mol) are run in slowly with vigorous stirring. The mixture is stirred for 15 minutes before commencing the dropwise addition, over 30 minutes, of 116.8 g (0.575 mol) of 3-bromomethylheptane. The reaction is continued at 100 C. for about 12 hours. The thin-layer chromatogram indicates virtually quantitative conversion. Solvent and excess bromide are removed in vacuo and the residue (an oil) is taken up in 500 ml of toluene. The mixture is subjected three times to extraction by shaking with water and the extracts are dried over sodium sulfate and concentrated to dryness. High-vacuum distillation via a 10 cm Vigreux column (127-132 C., 0.15 mm) gives 97.5 g (84% of theory) of 4-(2-ethylhexyloxy)benzonitrile as a coloured oil.

後処理

  1. customfitted with stirrer, condenser
  2. temperatureThe batch is heated to 80 C
  3. additionthe dropwise addition
  4. waitover 30 minutes
  5. waitfor about 12 hours
  6. customSolvent and excess bromide are removed in vacuo
  7. extractionto extraction
  8. stirringby shaking with water
  9. dry with materialthe extracts are dried over sodium sulfate
  10. concentrationconcentrated to dryness
  11. distillationHigh-vacuum distillation via a 10 cm Vigreux column (127-132 C., 0.15 mm)

出典と根拠

ORDレコード
ord-a1b80078c95f4ed283cbddb653187b83
出典データセット
uspto-grants-1997_11
特許番号
US05688995

関連ノート

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