Phenol → 1-(4-chlorophenyl)-2-phenoxyethanone

HRID 482603Notes

Reaction equation

HRID 482603 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1([OH:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)=[O:17]>C(C(C)=O)C>[O:13]([CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 68303p-Chlorophenacyl bromide

Product 1

HCID 14715261-(4-chlorophenyl)-2-phenoxyethanoneYield 50.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To 28.4 g (213 mmole) of anhydrous potassium carbonate suspended in 100 ml of methyl ethyl ketone was added 20 g (213 mmole) of phenol and 47 g (201 mmole) of 2-bromo-4'-chloroacetophenone. The reaction mixture was refluxed for 2.5 hours, cooled, concentrated in vacuo, partitioned between diethyl ether and water, washed with dilute aqueous sodium hydroxide, washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to yield 25 g of 2-phenoxy-4'-chloroacetophenone, a white solid, mp 80°-83° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 2.5 hours
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. custompartitioned between diethyl ether and water
  5. washwashed with dilute aqueous sodium hydroxide
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-50b1d6e6d59a4673ab86e3f631fbb60e
Source dataset
uspto-grants-1998_08
Patent number
US05798311

Reaction notes

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