Chloroacetonitrile → 3,4-Dimethoxyphenoxyacetonitrile

HRID 458792Notes

Reaction equation

HRID 458792 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl[CH2:13][C:14]#[N:15].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O.CCCCCC>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[O:11][CH2:13][C:14]#[N:15]

Participants

6

Reactant 4

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 162513,4-DimethoxyphenolHCID 21226206Ethyl acetate hexane

Product 1

HCID 189913533,4-DimethoxyphenoxyacetonitrileYield 71.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3,4-dimethoxyphenol (5.0 g, 32.4 mmol) in dry acetone (160 ml), were added chloroacetonitrile (2.05 ml, 32.4 mmol) and anhydrous K2CO3 (6.72 g, 48.6 mmol). The reaction mixture was stirred at reflux for 20 h under nitrogen. After cooling, the mixture was filtered and concentrated in vacuo. The residue was combined with H2O, extracted with CH2Cl2, and the combined organic phases were dried over anhydrous MgSO4, filtered and concentrated to give a crude oil. Flash chromatography (AcOEt/hexane: 3/7) gave the title product (4.5 g, 68%).

Workup

  1. temperatureat reflux for 20 h under nitrogen
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. concentrationconcentrated in vacuo
  5. extractionextracted with CH2Cl2
  6. dry with materialthe combined organic phases were dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a crude oil

Sources & evidence

ORD record
ord-8816e7b744094312af3b119e1ef6e794
Source dataset
uspto-grants-2007_03
Patent number
US07192950B2

Reaction notes

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