Chloroacetone → 1-(4-Fluorophenoxy)propan-2-one

HRID 985556Notes

Reaction equation

HRID 985556 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:16][C:17](=[O:19])[CH3:18]>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:16][C:17](=[O:19])[CH3:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 97324-FluorophenolHCID 11430Potassium Carbonate

Product 1

HCID 128146941-(4-Fluorophenoxy)propan-2-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of para-fluorophenol (15 g) and K2CO3 (18.5 g) in 100 mL acetone were added chloroacetone (10.4 mL) and of KI (22 g). After heating at reflux for 18 h the reaction mixture was cooled down and left at RT overnight. The reaction mixture was filtered, washed with acetone, and evaporated to dryness. The residue was partitioned between dichloromethane and water, the organic layer was separated and washed with water, dried over MgSO4, and evaporated to yield 15 g of 1-(4-fluoro-phenoxy)-propan-2-one as a yellow liquid.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 18 h the reaction mixture
  3. temperaturewas cooled down
  4. filtrationThe reaction mixture was filtered
  5. washwashed with acetone
  6. customevaporated to dryness
  7. customThe residue was partitioned between dichloromethane and water
  8. customthe organic layer was separated
  9. washwashed with water
  10. dry with materialdried over MgSO4
  11. customevaporated

Sources & evidence

ORD record
ord-a8f38012c0884afebd4bb11be6720bf0
Source dataset
uspto-grants-2005_03
Patent number
US06872744B2

Reaction notes

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