4-Chlorophenol → 1-(p-Chlorophenoxy)-3,3-dimethyl-4-chloro-2-butanone

HRID 126877Notes

Reaction equation

HRID 126877 reaction equation
Br[CH2:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][Cl:6].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:6][CH2:5][C:4]([CH3:8])([CH3:7])[C:3](=[O:9])[CH2:2][O:17][C:14]1[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 104207672-Butanone, 1-bromo-4-chloro-3,3-dimethyl-

Product 1

HCID 201382951-(p-Chlorophenoxy)-3,3-dimethyl-4-chloro-2-butanoneYield 80.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

213.5 g (1 mol) of 1-bromo-4-chloro-3,3-dimethyl-butan-2-one were added dropwise to a boiling suspension of 128.5 g (1 mol) of 4-chlorophenol and 140 g (1 mol) of potassium carbonate in 1,000 ml of absolute acetone. The mixture was stirred under reflux for 15 hours and then allowed to cool and the inorganic residue was filtered off and rinsed with acetone. The filtrate was concentrated by distilling off the solvent in vacuo, the residue was taken up in 1,000 ml of methylene chloride and the methylene chloride mixture was washed three times with 250 ml of water each time, dried over sodium sulphate and distilled. 210 g (80.7% of theory) of 4-chloro-1-(4-chlorophenoxy)-3,3-dimethyl-butan-2-one of boiling point 125°-127° C./0.1 mm were obtained.

Workup

  1. temperatureunder reflux for 15 hours
  2. temperatureto cool
  3. filtrationthe inorganic residue was filtered off
  4. washrinsed with acetone
  5. concentrationThe filtrate was concentrated
  6. distillationby distilling off the solvent in vacuo
  7. washthe methylene chloride mixture was washed three times with 250 ml of water each time
  8. dry with materialdried over sodium sulphate
  9. distillationdistilled

Sources & evidence

ORD record
ord-8ed1ffc6bae54fa19ff776cae9dfd5dc
Source dataset
uspto-grants-1981_03
Patent number
US04254132

Reaction notes

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