Potassium Cyanide → 2-(3,5-Dichlorophenyl)acetonitrile

HRID 234936

Reaction equation

HRID 234936 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH2:5]Cl.[C-:11]#[N:12].[K+]>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][C:11]#[N:12])[CH:7]=[C:8]([Cl:10])[CH:9]=1

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 1378803,5-Dichlorobenzyl chloride

Product 1

HCID 126899782-(3,5-Dichlorophenyl)acetonitrile

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a vigorously stirred solution of 3,5-dichlorobenzylchloride (28 g) in dichloromethane (150 ml) was added a mixture of KCN (27.5 g) and tetrabutylammonium hydrogen sulphate (2.38 g) in water (110 ml). After stirring at room temperature for 22 hours, the mixture was diluted with dichloromethane, the organic phase washed with water and concentrated in vacuo to leave an oil. Filtration through silica with toluene followed by concentration then trituration with hexane gave the desired product as a colourless solid. 15.8 g, mp. 31°-32° C.

Workup

  1. washthe organic phase washed with water
  2. concentrationconcentrated in vacuo
  3. customto leave an oil
  4. filtrationFiltration through silica with toluene
  5. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-a2fcd0071a234bf79414e8030e9ac48a
Source dataset
uspto-grants-1997_01
Patent number
US05597827

Linked notes

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