Chloroethane → Benzeneacetonitrile, .alpha.-ethyl-

HRID 596917Notes

Reaction equation

HRID 596917 reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10](Cl)[CH3:11].[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[C:1]1([CH:7]([CH2:10][CH3:11])[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6337ChloroethaneHCID 8794Phenylacetonitrile2×HCID 14798Sodium Hydroxide

Product 1

HCID 95334Benzeneacetonitrile, .alpha.-ethyl-Yield 90%

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Procedure

Makosza et al. also studied the alkylation of phenylacetonitrile using quaternary ammonium salts as a catalyst, but satisfactory yields and purity could not be obtained. For example, they reported in Roczniki Chem. Vol. 39, 1223 (1965) and Chemical Abstracts Vol. 64, 12595 (1965) that when phenylacetonitrile is alkylated at room temperature with ethyl chloride in the presence of a 50% aqueous sodium hydroxide solution using benzyltriethyl ammonium chloride as a catalyst, 2-phenylbutyronitrile is obtained at a yield of 90%. The purity of the product was not disclosed, however.

Workup

  1. customsatisfactory yields
  2. custompurity could not be obtained

Sources & evidence

ORD record
ord-5108cdf3322045759584170f268211ae
Source dataset
uspto-grants-1977_03
Patent number
US04012428

Reaction notes

Loading…