4-Chlorophenol → 1-(4-Chlorophenoxy)-3-methylbutan-2-one

HRID 1380985Notes

Reaction equation

HRID 1380985 reaction equation
Br[CH2:2][C:3](=[O:7])[CH:4]([CH3:6])[CH3:5].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:2][C:3](=[O:7])[CH:4]([CH3:6])[CH3:5])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 108990371-Bromo-3-methylbutan-2-one

Product 1

HCID 134736211-(4-Chlorophenoxy)-3-methylbutan-2-oneYield 74%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

338 g (2.77 mols) of 1-bromo-3-methyl-butan-2-one were rapidly added dropwise to a mixture of 357 g (2.78 mols) of 4-chlorophenol and 483 g (3.5 mols) of potassium carbonate in 2.5 liters of methyl ethyl ketone. The mixture was heated under reflux for 16 hours and then filtered. The filtrate was concentrated by stripping off the solvent under reduced pressure, the residue was taken up in methylene chloride and the organic phase was washed twice with 2N aqueous sodium hydroxide solution, once with water and once with saturated aqueous sodium chloride solution. After drying, the organic phase was concentrated by stripping off the solvent. The residue which remained was distilled under a high vacuum. 435 g (74% of theory) of 1-(4-chlorophenoxy)-3-methyl-butan-2-one were obtained in this manner.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 16 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. washthe organic phase was washed twice with 2N aqueous sodium hydroxide solution, once with water and once with saturated aqueous sodium chloride solution
  6. customAfter drying
  7. concentrationthe organic phase was concentrated
  8. distillationThe residue which remained was distilled under a high vacuum

Sources & evidence

ORD record
ord-110beac42c8444d9845d14336f66a7ea
Source dataset
uspto-grants-1986_04
Patent number
US04584373

Reaction notes

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