Potassium Cyanide → 4-Biphenylacetonitrile

HRID 964596

Reaction equation

HRID 964596 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 (2.6g) was added to a stirred, two-phase mixture of 4-(chloromethyl)biphenyl (2.02g) 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 (MgS04) and evaporated to give a solid residue which was crystallised from n-hexane to give 4-(cyanomethyl)biphenyl (1.3g) as a solid, m.p. 95° C.; microanalysis, found: C, 86.3; H, 5.7; N, 7.2%; C14H11N .O.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. customdried (MgS04)
  4. customevaporated
  5. customto give a solid residue which
  6. customwas crystallised from n-hexane

Sources & evidence

ORD record
ord-08baa463e22241db85abdbcd11810cd7
Source dataset
uspto-grants-1998_06
Patent number
US05770608

Linked notes

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