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

HRID 2294672

반응식

HRID 2294672 반응식
[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]

참가 물질

5

반응물 3

HCID 130194-CyanophenolHCID 14798Sodium HydroxideHCID 868042-Ethylhexyl bromide

생성물 1

HCID 190861874-(2-Ethylhexyloxy)benzonitrile수율 84.3%

시약·촉매·용매 1

HCID 80192-Methoxyethanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a1b80078c95f4ed283cbddb653187b83
출처 데이터셋
uspto-grants-1997_11
특허 번호
US05688995

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