2,4-Dichlorophenol → 1-(2,4-Dichlorophenoxy)-3,3-dimethyl-4-fluoro-2-butanone

HRID 904648Notes

Reaction equation

HRID 904648 reaction equation
Br[CH2:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][F:6].C(=O)([O-])[O-].[K+].[K+].[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[OH:24]>CC(C)=O>[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[O:24][CH2:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][F:6]

Participants

5

Reactant 3

HCID 84492,4-DichlorophenolHCID 11430Potassium CarbonateHCID 130194421-Bromo-3,3-dimethyl-4-fluoro-2-butanone

Product 1

HCID 130194431-(2,4-Dichlorophenoxy)-3,3-dimethyl-4-fluoro-2-butanoneYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 197 g (1 mol) of 1-bromo-3,3-dimethyl-4-fluoro-2-butanone in 100 ml of acetone was added dropwise, at the boiling point, to 140 g (1 mol) of potassium carbonate and 163 g (1 mol) of 2,4-dichlorophenol in 1,000 ml of acetone. The mixture was stirred under reflux for 20 hours, cooled and filtered. The filtrate was concentrated by distilling off the acetone under a waterpump vacuum. The residue was dissolved in 500 ml of toluene, washed with 500 ml of 10% strength sodium hydroxide solution and with two 250 ml portions of water, dried over sodium sulphate and concentrated by distilling off the toluene under a waterpump vacuum. 244.6 g (88% of theory) of 1-(2,4-dichlorophenoxy)-3,3-dimethyl-4-fluoro-2-butanone were obtained as a highly viscous oil which could be further reacted in crude form.

Workup

  1. temperatureunder reflux for 20 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. distillationby distilling off the acetone under a waterpump vacuum
  6. dissolutionThe residue was dissolved in 500 ml of toluene
  7. washwashed with 500 ml of 10% strength sodium hydroxide solution and with two 250 ml portions of water
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated
  10. distillationby distilling off the toluene under a waterpump vacuum

Sources & evidence

ORD record
ord-863e67b5e218485582c81e7b30d607c0
Source dataset
uspto-grants-1983_12
Patent number
US04419361

Reaction notes

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