Acrylonitrile → 3-(4-Fluorophenoxy)propanenitrile

HRID 1732110Notes

Reaction equation

HRID 1732110 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]>C(N(CC)CC)C>[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

4

Reactant 2

HCID 7855AcrylonitrileHCID 97324-Fluorophenol

Product 1

HCID 30204753-(4-Fluorophenoxy)propanenitrileYield 70%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 11.2 g of 4-fluorophenol, 10.6 g of acrylonitrile and 2.02 g of triethylamine was refluxed for 16 hours with stirring and then acrylonitrile, triethylamine and 4-fluorophenol were removed under reduced pressure. The obtained residue was diluted with ether, washed successively with 10% aqueous solution of sodium hydroxide and 2N hydrochloric acid and dehydrated with anhydrous magnesium sulfate. Ether was distilled away to give 11.51 g of colorless liquid of 3-(4-fluorophenoxy)propionitrile (yield: 70%).

Workup

  1. temperaturewas refluxed for 16 hours
  2. customacrylonitrile, triethylamine and 4-fluorophenol were removed under reduced pressure
  3. additionThe obtained residue was diluted with ether
  4. washwashed successively with 10% aqueous solution of sodium hydroxide and 2N hydrochloric acid
  5. distillationEther was distilled away

Sources & evidence

ORD record
ord-91d9ca2a3f6a48e98ec21a2668aad93d
Source dataset
uspto-grants-1986_11
Patent number
US04625042

Reaction notes

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