Ethanol → 4-(Octyloxy)benzonitrile

HRID 1081522Notes

Reaction equation

HRID 1081522 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH2:10](Br)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[OH-].[K+].C(O)C>O>[CH2:10]([O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 702EthanolHCID 81401-BromooctaneHCID 130194-CyanophenolHCID 14797Potassium Hydroxide

Product 1

HCID 1451614-(Octyloxy)benzonitrileYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1-liter round bottom flask was charged with 50 g of p-hydroxybenzonitrile, 89.2 g of octyl bromide, 23.5 g of potassium hydroxide and 500 ml of ethanol. A calcium chloride tube was attached to the flask and the content was refluxed for 4 hours. Then, one liter of water was added into the flask, followed by extraction with 1300 ml of dichloromethane. The extract was washed with water and dried over anhydrous sodium sulfate. After distilling the solvent off, the remaining system was purified by means of silica gel column chromatography to provide 80.6 g of 4-octyloxybenzonitrile (Compound A).

Workup

  1. customA calcium chloride tube was attached to the flask
  2. temperaturethe content was refluxed for 4 hours
  3. extractionfollowed by extraction with 1300 ml of dichloromethane
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationAfter distilling the solvent off, the remaining system
  7. customwas purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-54f2f1187e024bc0bd8b8521cdb43918
Source dataset
uspto-grants-1996_12
Patent number
US05587106

Reaction notes

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