4-Chlorophenol → 1-[2-Chloro-4-(4-chlorophenoxy)phenyl]ethan-1-one

HRID 1770359Notes

Reaction equation

HRID 1770359 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][C:10]([C:12]1[CH:17]=[CH:16][C:15](F)=[CH:14][C:13]=1[Cl:19])=[O:11].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:19][C:13]1[CH:14]=[C:15]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:16]=[CH:17][C:12]=1[C:10](=[O:11])[CH3:9]

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 27365072'-Chloro-4'-fluoroacetophenone

Product 1

HCID 6774791-[2-Chloro-4-(4-chlorophenoxy)phenyl]ethan-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-chlorophenol (186 g), 2-chloro-4-fluoroacetophenone (250 g) and potassium carbonate (238 g) in DMF (960 mL) was heated to reflux for 48 h. After cooling to room temperature, the reaction mixture was partitioned between MTBE and water and the aqueous phase was extracted twice with MTBE. The combined organic phases were consecutively washed with 10% LiCl solution, dil. NaOH solution and water and dried. The solvent was evaporated under reduced pressure and the crude material was crystallized from diisopropyl ether.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 48 h
  3. customthe reaction mixture was partitioned between MTBE and water
  4. extractionthe aqueous phase was extracted twice with MTBE
  5. washThe combined organic phases were consecutively washed with 10% LiCl solution, dil. NaOH solution and water
  6. customdried
  7. customThe solvent was evaporated under reduced pressure
  8. customthe crude material was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-5dbccbc3503245d396ae24743e35c3ed
Source dataset
uspto-grants-2016_02
Patent number
US09247746B2

Reaction notes

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