Potassium Cyanide → 4-Biphenylacetonitrile

HRID 2256074Notes

Reaction equation

HRID 2256074 reaction equation
[C-:1]#[N:2].[K+].Cl[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[C:1]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)#[N:2]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 154634-Phenylbenzyl chloride

Product 1

HCID 358564-BiphenylacetonitrileYield 67.5%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

Potassium cyanide (2.6 g) was added to a stirred, two-phase mixture of 4-(chloromethyl)biphenyl (2.02 g) and tetrabutyl ammonium hydrogen sulphate (200 mg) in dichloromethane (50 ml). The reaction mixture was stirred at ambient temperature for 36 hours. The organic layer was separated and washed with water (10 ml), dried (MgSO4) and evaporated to give a solid residue which was crystallised from n-hexane to give 4-(cyanomethyl)biphenyl (1.3 g) as a solid, m.p. 95° C.; microanalysis, found: C, 86.3; H, 5.7; N, 7.2%; C14H11N .0.1H2O requires C, 86.2; H, 5.7; N, 7.18%.

Workup

  1. customThe organic layer was separated
  2. washwashed with water (10 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a solid residue which
  6. customwas crystallised from n-hexane

Sources & evidence

ORD record
ord-17c3c6b833aa432497b1a3ca4d803d52
Source dataset
uspto-grants-1997_08
Patent number
US05654315

Reaction notes

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