Sodium Cyanide → (4-tert-Butylphenyl)acetonitrile

HRID 2363086Notes

Reaction equation

HRID 2363086 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9]Br)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C-:13]#[N:14].[Na+]>C(O)C.O>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][C:13]#[N:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

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

Product 1

HCID 76784(4-tert-Butylphenyl)acetonitrileYield 115.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-t-Butylbenzylbromide (903 mg, 3.98 mmol) was reacted with NaCN (210 mg, 4.30 mmol) in ethanol (10 ml) and H2O (2 ml) at 80° C. The reaction solvent was removed in vacuo. The residue was diluted with EtOAc and H2O and the aqueous layer was extracted with EtOAc. The combined organic layer was dried over MgSO4 and then concentrated in vacuo. The residue was purified with column chromatography to yield title compound (797 mg)

Workup

  1. customThe reaction solvent was removed in vacuo
  2. additionThe residue was diluted with EtOAc and H2O
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified with column chromatography

Sources & evidence

ORD record
ord-08703d1572f24f2183bde874197ea58f
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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