Acrylonitrile → 3-(4-Fluorophenoxy)propanenitrile

HRID 1732109Notes

Reaction equation

HRID 1732109 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9](#[N:12])[CH:10]=[CH2:11]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:11][CH2:10][C:9]#[N:12])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7855AcrylonitrileHCID 97324-Fluorophenol

Product 1

HCID 30204753-(4-Fluorophenoxy)propanenitrileYield 85%

Procedure

A mixture of 11.2 g of 4-fluorophenol, 26.5 g of acrylonitrile and 4.9 g of cupric hydroxide was refluxed for 8 hours with stirring, and then acrylonitrile and 4-fluorophenol were removed from the mixture under reduced pressure. After diluting the obtained residue with ether and filtering solid, the ether layer was successively washed with 10% aqueous solution of sodium hydroxide and 2N hydrochloric acid and dehydrated with anhydrous magnesium sulfate. Ether was distilled away to give 14.02 g of colorless liquid of 3-(4-fluorophenoxy)propionitrile (yield: 85%).

Workup

  1. temperaturewas refluxed for 8 hours
  2. customacrylonitrile and 4-fluorophenol were removed from the mixture under reduced pressure
  3. additionAfter diluting the obtained residue with ether
  4. filtrationfiltering solid
  5. washthe ether layer was successively washed with 10% aqueous solution of sodium hydroxide and 2N hydrochloric acid
  6. distillationEther was distilled away

Sources & evidence

ORD record
ord-48a8d989692e4912b071e834d625507c
Source dataset
uspto-grants-1986_11
Patent number
US04625042

Reaction notes

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