1-Bromooctane → 4-(Octyloxy)benzonitrile

HRID 344799Notes

Reaction equation

HRID 344799 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].C(=O)([O-])[O-].[K+].[K+]>CC(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

5

Reactant 3

HCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 130194-Cyanophenol

Product 1

HCID 1451614-(Octyloxy)benzonitrileYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 4000 ml of acetone was dissolved 500 g (4.2 moles) of p-hydroxybenzonitrile and 965 g (5.0 moles) of octyl bromide, 828 g (6.0 moles) of anhydrous potassium carbonate was added thereto, and the mixture was refluxed with heating for 30 hours. Then, the inorganic salt was filtered off from the reaction mixture, acetone was distilled under reduced pressure. To the residue was added 2000 ml of ether and the mixture was washed with 2N aqueous solution of sodium hydroxide, water, then saturated aqueous solution of sodium chloride. The resulting organic layer was dried with anhydrous magnesium sulfate, and ether was distilled under reduced pressure to give 855 g of p-octyloxybenzonitrile (yield: 88%).

Workup

  1. additionwas added
  2. temperaturethe mixture was refluxed
  3. temperaturewith heating for 30 hours
  4. filtrationThen, the inorganic salt was filtered off from the reaction mixture, acetone
  5. distillationwas distilled under reduced pressure
  6. additionTo the residue was added 2000 ml of ether
  7. washthe mixture was washed with 2N aqueous solution of sodium hydroxide, water
  8. dry with materialThe resulting organic layer was dried with anhydrous magnesium sulfate, and ether
  9. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-838b0e67848640dc98e8615ae70919ee
Source dataset
uspto-grants-1991_10
Patent number
US05053507

Reaction notes

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