4-Chlorophenol → HCID 23350027, compound

HRID 262450Notes

Reaction equation

HRID 262450 reaction equation
[C:1]([O:4][CH2:5][C:6]([CH3:12])([CH3:11])[C:7](=[O:10])[CH2:8]Br)(=[O:3])[CH3:2].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([O:4][CH2:5][C:6]([CH3:12])([CH3:11])[C:7](=[O:10])[CH2:8][O:20][C:17]1[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 23350035HCID 23350035, compound

Product 1

HCID 23350027HCID 23350027, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

170 g (0.72 mol) of 4-acetoxy-1-bromo-3,3-dimethylbutan-2-one in 200 ml of acetone were added dropwise, over the course of 100 minutes, to a suspension of 92.1 g (0.72 mol) of 4-chlorophenol and 108 g (0.72 mol) of potassium carbonate in 1,000 ml of acetone. After heating for 15 hours whilst stirring under reflux, the mixture was filtered and the filtrate was concentrated by distilling off the solvent in vacuo. The residue was taken up in 200 ml of methylene chloride and the solution was washed three times with 50 ml of water at a time, dried over sodium sulphate and concentrated. The oily residue was distilled. 153 g (72% of theory) of 4-acetoxy-1-(4-chlorophenoxy)-3,3-dimethyl-butan-2-one of boiling point 140°-145° C./0.2 mm Hg was obtained.

Workup

  1. temperatureAfter heating for 15 hours
  2. temperatureunder reflux
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. distillationby distilling off the solvent in vacuo
  6. washthe solution was washed three times with 50 ml of water at a time
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated
  9. distillationThe oily residue was distilled

Sources & evidence

ORD record
ord-0fde3cc70403453f8c05507f1ebe1c67
Source dataset
uspto-grants-1979_05
Patent number
US04154842

Reaction notes

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