Potassium Carbonate → 4-[(But-3-en-1-yl)oxy]benzonitrile

HRID 1743727Notes

Reaction equation

HRID 1743727 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:17][CH2:18][CH:19]=[CH2:20]>>[CH2:20]([O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[CH2:19][CH:18]=[CH2:17]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 21241Homoallyl bromide

Product 1

HCID 139723854-[(But-3-en-1-yl)oxy]benzonitrileYield 85.4%

Procedure

4-Cyanophenol (30 g, 250 mmol) was mixed with K2CO3 (72.5 g, 525 mmol) and stirred for 60 minutes. 4-Bromo-1-butene (50 g, 370 mmol) was added dropwise. The reaction mixture was stirred at 60° C. overnight. The solids were filtered off and the solvents were evaporated. The residue was dissolved in DCM. and washed with 1 N NaOH. The organic layer was separated, dried (Na2SO4) and evaporated to give 37 g (58%) of the sub-title compound.

Workup

  1. stirringThe reaction mixture was stirred at 60° C. overnight
  2. filtrationThe solids were filtered off
  3. customthe solvents were evaporated
  4. dissolutionThe residue was dissolved in DCM
  5. washand washed with 1 N NaOH
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-d7b609c5cb5944e9898a36f410529637
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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