Allyl bromide → 4-(ALLYLOXY)BENZONITRILE

HRID 2294969Notes

Reaction equation

HRID 2294969 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]>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

4

Reactant 2

HCID 7841Allyl bromideHCID 130194-Cyanophenol

Product 1

HCID 2579494-(ALLYLOXY)BENZONITRILE

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-cyanophenol (50 g), allyl bromide (27.2 ml) potassium carbonate (47.8 g) in acetone (100 ml) was heated at reflux for 16 hours. The reaction mixture was evaporated, water was added to the residue and the aqueous mixture was extracted with diethyl ether. The diethyl ether extract was washed with dilute aqueous sodium hydroxide solution, dried (MgSO4) and evaporated to give 4-cyanophenyl allyl ether as a solid, m.p. 41.6° C.; microanalysis, found: C, 75.1; H, 5.8; N, 8.7%; C10H9NO2 requires: C, 75.5; H, 5-7; N, 8.8%; NMR: 4.55-4.65(2H,m), 5.2-5.4(2H,m), 5.9-6.05(1H,m), 7.0-7.1(2H,m) and 7.65-7.75(2H,m).

Workup

  1. temperatureat reflux for 16 hours
  2. customThe reaction mixture was evaporated
  3. additionwater was added to the residue
  4. extractionthe aqueous mixture was extracted with diethyl ether
  5. extractionThe diethyl ether extract
  6. washwas washed with dilute aqueous sodium hydroxide solution
  7. dry with materialdried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-f2b8299f0996402c9b9d11ec0351f35c
Source dataset
uspto-grants-1997_11
Patent number
US05691349

Reaction notes

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