Cyanide → (3-Methoxy-5-methylphenyl)acetonitrile

HRID 1383354Notes

Reaction equation

HRID 1383354 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([O:10][CH3:11])[CH:6]=[C:7]([CH3:9])[CH:8]=1.[C-]#N.[Na+].[C-]#N.C[C:18]#[N:19]>CS(C)=O>[CH3:11][O:10][C:5]1[CH:4]=[C:3]([CH2:2][C:18]#[N:19])[CH:8]=[C:7]([CH3:9])[CH:6]=1

Participants

6

Reactant 4

HCID 5975CyanideHCID 6342AcetonitrileHCID 8929Sodium CyanideHCID 5855341-(Bromomethyl)-3-methoxy-5-methylbenzene

Product 1

HCID 22048241(3-Methoxy-5-methylphenyl)acetonitrileYield 70%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-bromomethyl-5-methylanisole (17 g; 0.008 mol; from step (i) above) in DMSO (25 mL) was added NaCN (8.2 g; 0.16 mol). The mixture, which became very warm upon the addition of the cyanide, was left to cool to room temperature over 1 hour. CH3CN (25 mL) was then added, and the mixture refluxed for 1 hour. The reaction mixture was concentrated, water (200 mL) was added, and the resultant solution was extracted 3 times with ether. The combined organic phase was washed with water, dried (Na2SO4), and concentrated to give 9 g (70%) of the sub-title product as a yellow oil, which was used without further purification in the next step.

Workup

  1. waitwas left
  2. temperaturethe mixture refluxed for 1 hour
  3. concentrationThe reaction mixture was concentrated
  4. additionwater (200 mL) was added
  5. extractionthe resultant solution was extracted 3 times with ether
  6. washThe combined organic phase was washed with water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a2876a9bb9e343ba9789d6391afad9eb
Source dataset
uspto-grants-2001_07
Patent number
US06255301B1

Reaction notes

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