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

HRID 2286765Notes

Reaction equation

HRID 2286765 reaction equation
Br[CH2:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][F: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:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][F:6])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 130194421-Bromo-3,3-dimethyl-4-fluoro-2-butanone

Product 1

HCID 221632321-(4-Chlorophenoxy)-3,3-dimethyl-4-fluoro-2-butanoneYield 90.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
20 °C

Procedure

157 g (0.79 mol) of 1-bromo-3,3-dimethyl-4-fluoro-2-butanone were added dropwise to a stirred mixture of 102 g (0.79 mol) of p-chlorophenol and 110 g (0.79 mol) of powered potassium carbonate in 500 ml of acetone at 20° to 30° C., while cooling. The mixture was subsequently stirred at 20° C. for 2 hours, the inorganic salt was filtered off and the filtrate was concentrated. The residue was distilled under a high vacuum. 175 g (90% of theory) of 1-(4-chlorophenoxy)-3,3-dimethyl-4-fluoro-2-butanone of boiling point 112° to 119° C./0.05 mm Hg were obtained. ##STR15##

Workup

  1. temperaturewhile cooling
  2. filtrationthe inorganic salt was filtered off
  3. concentrationthe filtrate was concentrated
  4. distillationThe residue was distilled under a high vacuum

Sources & evidence

ORD record
ord-8de8a39ae1224504b75418f52e1050bf
Source dataset
uspto-grants-1981_05
Patent number
US04267381

Reaction notes

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