Benzyl Chloride → 4-Benzyloxybenzonitrile

HRID 1074110Notes

Reaction equation

HRID 1074110 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].[CH2:10](Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:10]([O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 130194-Cyanophenol

Product 1

HCID 5613714-BenzyloxybenzonitrileYield 84.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Cyanophenol (95.2 g), benzyl chloride (127 g) and potassium carbonate (138 g) are refluxed in acetone (160 ml) for 5 hours. The product is separated by filtration, concentrated under reduced pressure, and thereto is added benzene. The mixture is washed with water, and benzene is distilled off under reduced pressure to give 4-benzyloxybenzonitrile (141.38 g). The 4-benzyloxybenzonitrile (141 g) is dissolved in benzene (338 ml) and thereto is added ethanol (270 ml), and the mixture is cooled to 0° C. Into the resulting slurry is bubbled hydrogen chloride gas (36 liters) with stirring, and thereafter, the temperature is raised to 25° C., and the mixture is allowed to stand for 2 days. The reaction mixture is concentrated under reduced pressure until 1/3volume, and to the concentrated mixture is added ether. The precipitated crystals are separated by suction filtration to give an imide ester (183 g).

Workup

  1. customThe product is separated by filtration
  2. concentrationconcentrated under reduced pressure
  3. additionis added benzene
  4. washThe mixture is washed with water, and benzene
  5. distillationis distilled off under reduced pressure

Sources & evidence

ORD record
ord-e1f6982a69b14188862a7db03ff6b353
Source dataset
uspto-grants-1990_11
Patent number
US04973425

Reaction notes

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