Sodium Cyanide → 2-(3,4-Dimethylphenyl)acetonitrile

HRID 985565Notes

Reaction equation

HRID 985565 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[CH2:5]Cl.[C-:11]#[N:12].[Na+]>CN(C)C=O.O>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:5][C:11]#[N:12])[CH:7]=[CH:8][C:9]=1[CH3:10]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 660183,4-Dimethylbenzyl chloride

Product 1

HCID 764012-(3,4-Dimethylphenyl)acetonitrileYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture solution of 3,4-dimethylbenzyl chloride 10 g (64.7 mmol) in dimethyl formamide (15 ml) was treated with sodium cyanide (15.85 g, 323.8 mmol) for 16 hrs at 100° C. The mixture was diluted with H2O and extracted with CH2Cl2 several times. The combined organic layers were washed with H2O, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with EtOAc/hexanes (1:10) as an eluant to give compound 2.

Workup

  1. extractionextracted with CH2Cl2 several times
  2. washThe combined organic layers were washed with H2O
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel with EtOAc/hexanes (1:10) as an eluant

Sources & evidence

ORD record
ord-3a56ffa03e68447a95b104a240f1ed7b
Source dataset
uspto-grants-2005_03
Patent number
US06872748B2

Reaction notes

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