Sodium Cyanide → (4-tert-Butylphenyl)acetonitrile

HRID 1740366Notes

Reaction equation

HRID 1740366 reaction equation
[C-:1]#[N:2].[Na+].[C:4]([C:8]1[CH:15]=[CH:14][C:11]([CH2:12]Br)=[CH:10][CH:9]=1)([CH3:7])([CH3:6])[CH3:5]>C(O)C.O.O>[C:4]([C:8]1[CH:15]=[CH:14][C:11]([CH2:12][C:1]#[N:2])=[CH:10][CH:9]=1)([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzene

Product 1

HCID 76784(4-tert-Butylphenyl)acetonitrileYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

Sodium cyanide (1.07 g, 22 mmol) was added to a stirred solution of 4-t-butylbenzylbromide (5 g, 22 mmol) in a mixture of EtOH-H2O (6:1) (70 mL). The reaction mixture was allowed to stir under reflux conditions for 4 hours. After cooling the mixture to room temperature, the solvent was evaporated under reduced pressure to afford a yellow oil. The oil was suspended in water (20 mL) and extracted with ether (3×25 mL). The solvent was removed under reduced pressure to give a yellow oil which was purified by distillation (Kugelrohr, bp 120-125° C., 0.2 mm Hg) to afford 3.37 g (89%) of the title compound as a colorless oil.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customto afford a yellow oil
  3. extractionextracted with ether (3×25 mL)
  4. customThe solvent was removed under reduced pressure
  5. customto give a yellow oil which
  6. distillationwas purified by distillation (Kugelrohr, bp 120-125° C., 0.2 mm Hg)

Sources & evidence

ORD record
ord-12b5b706664049b99325e275ddf9afdd
Source dataset
uspto-grants-1999_10
Patent number
US05969137

Reaction notes

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