Acrylonitrile → Benzeneacetonitrile, 4-fluoro-

HRID 2059211Notes

Reaction equation

HRID 2059211 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[C:11](#[N:14])[CH:12]=[CH2:13].C[O-].[Na+]>CO.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[F:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]([CH2:13][CH2:12][C:11]#[N:14])[C:7]#[N:8])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 7855AcrylonitrileHCID 68016Benzeneacetonitrile, 4-fluoro-HCID 10942334Sodium Methoxide3×

Product 2

HCID 68016Benzeneacetonitrile, 4-fluoro-HCID 13034553HCID 13034553, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Twenty-five g of 4-fluorobenzylcyanide is mixed with approximately 3.5 ml of freshly distilled acrylonitrile in a suitable reaction vessel. To this stirred mixture is added dropwise a solution of 80 mg of sodium methoxide in 1 ml of methanol. When about half of the sodium methoxide is added, there is an exothermic reaction. After all the sodium methoxide is added, the mixture is kept on a steam-bath for 2 hours and is then dissolved in toluene and washed with water. The toluene is removed by evaporation and the residue is separated into its components by fractional distillation to give 18 g of 4-fluorobenzylcyanide, and 2 g of 2-(4-fluorophenyl)glutaronitrile, bp 118°-122° C. at 0.03 mm.

Workup

  1. customan exothermic reaction
  2. washwashed with water
  3. customThe toluene is removed by evaporation
  4. customthe residue is separated into its components by fractional distillation

Sources & evidence

ORD record
ord-91dab8cbe9f44438954fa034ca07d13b
Source dataset
uspto-grants-1982_03
Patent number
US04322421

Reaction notes

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