Potassium Carbonate → 2-(4-Chloro-2,6-dimethylphenoxy)acetonitrile

HRID 892170Notes

Reaction equation

HRID 892170 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.Br[CH2:12][C:13]#[N:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH2:12][C:13]#[N:14])=[C:4]([CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 707472,6-Dimethyl-4-chlorophenol

Product 1

HCID 222413682-(4-Chloro-2,6-dimethylphenoxy)acetonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Chloro-2,6-dimethylphenol (5.0 g, 32 mmol), bromoacetonitrile (2.2 mL, 32 mmol) and potassium carbonate (6.6 g, 48 mmol) are combined with acetone (50 mL) and heated at reflux for 18 h. The reaction is filtered, concentrated and the residue partitioned between dichloromethane and water. The organic phase is washed with 1N HCl and water and is then dried over magnesium sulfate, concentrated and purified by column chromatography (silica, 10% ethyl acetate in hexanes) to provide the title compound. MS (EI) 195 (M)+, Cl pattern.

Workup

  1. temperatureheated
  2. temperatureat reflux for 18 h
  3. filtrationThe reaction is filtered
  4. concentrationconcentrated
  5. customthe residue partitioned between dichloromethane and water
  6. washThe organic phase is washed with 1N HCl and water
  7. dry with materialis then dried over magnesium sulfate
  8. concentrationconcentrated
  9. custompurified by column chromatography (silica, 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-ccbd60a19f0a4f3fb55dd5fbe1138f26
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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