Sodium Cyanide → (3-Dimethoxymethyl-5-methyl-phenyl)-acetonitrile

HRID 426174Notes

Reaction equation

HRID 426174 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH:10]([O:13][CH3:14])[O:11][CH3:12])[CH:4]=1.[C-:15]#[N:16].[Na+]>CO>[CH3:12][O:11][CH:10]([O:13][CH3:14])[C:5]1[CH:4]=[C:3]([CH2:2][C:15]#[N:16])[CH:8]=[C:7]([CH3:9])[CH:6]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 591848751-Bromomethyl-3-dimethoxymethyl-5-methyl-benzene

Product 1

HCID 66705565(3-Dimethoxymethyl-5-methyl-phenyl)-acetonitrileYield 52.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-bromomethyl-3-dimethoxymethyl-5-methyl-benzene (6 g, 23 mmol) and sodium cyanide (1.7 g, 34 mmol) in methanol (30 ml) and distilled water (15 ml) was refluxed for 1.5 hr. After cooling to room temperature, the mixture was evaporated in vacuo and the residue was dissolved in ether, washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was then purified by silica gel column chromatography (eluent, ether:hexanes (1:3)) to afford 2.46 g (52%) of a colorless oil 1H NMR (300 MHz, CDCl3) δ 2.37 (3H, s), 3.33 (6H, s), 3.71 (2H, s), 5.33 (1H, s), 7.12 (1H, s), 7.20 (1H, s), 7.22 (1H, s).

Workup

  1. distillationdistilled water (15 ml)
  2. temperaturewas refluxed for 1.5 hr
  3. customthe mixture was evaporated in vacuo
  4. dissolutionthe residue was dissolved in ether
  5. washwashed with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was then purified by silica gel column chromatography (eluent, ether:hexanes (1:3))

Sources & evidence

ORD record
ord-3e25f131be404d3cb8b858c8b5545108
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

Loading…