Allyl bromide → 4-(ALLYLOXY)BENZONITRILE

HRID 2231671Notes

Reaction equation

HRID 2231671 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].[CH2:10](Br)[CH:11]=[CH2:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:12]([O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[CH:11]=[CH2:10]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 130194-Cyanophenol

Product 1

HCID 2579494-(ALLYLOXY)BENZONITRILEYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture comprising 29.75 g of 4-cyanophenol, 33.27 g of allyl bromide, 41.46 g of potassium carbonate and 350 ml of acetone, was refluxed under stirring for 4 hours. Acetone was distilled, and water was added to the residue. The mixture was extracted with benzene. The benzene layer was washed sequentially with a 5% sodium hydroxide aqueous solution and water, and dried over sodium sulfate. Then, the solvent was distilled off to obtain a pale yellow oily substance. The residual substance was crystallized from n-hexane-ethyl ether to obtain 38.16 g of 4-allyloxy benzonitrile as colorless crystals having a melting point of from 40.5° to 41° C.

Workup

  1. temperaturewas refluxed
  2. distillationAcetone was distilled
  3. additionwater was added to the residue
  4. extractionThe mixture was extracted with benzene
  5. washThe benzene layer was washed sequentially with a 5% sodium hydroxide aqueous solution and water
  6. dry with materialdried over sodium sulfate
  7. distillationThen, the solvent was distilled off
  8. customto obtain a pale yellow oily substance
  9. customThe residual substance was crystallized from n-hexane-ethyl ether

Sources & evidence

ORD record
ord-394c0f2782b044788ba171e7aa87b880
Source dataset
uspto-grants-1988_11
Patent number
US04783462

Reaction notes

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