4-Chlorophenol → 1-Chloro-4-(2-chloroethoxy)benzene

HRID 962460

Reaction equation

HRID 962460 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][Cl:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH2:11][Cl:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium Carbonate

Product 1

HCID 830341-Chloro-4-(2-chloroethoxy)benzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-chlorophenol (100 g), 1-bromo-2-chloroethane (335 g), potassium carbonate (129 g) and acetone (2 l) was boiled under reflux with stirring for 18 hours. The mixture was evaporated to dryness under reduced pressure and then dichloromethane was added to the cool residue. The mixture was filtered and the filtrate washed with 5M sodium hydroxide solution, water, dried, filtered and evaporated to give 2-chloroethyl 4-chlorophenyl ether as an oil.

Workup

  1. temperatureunder reflux
  2. customThe mixture was evaporated to dryness under reduced pressure
  3. additiondichloromethane was added to the cool residue
  4. filtrationThe mixture was filtered
  5. washthe filtrate washed with 5M sodium hydroxide solution, water
  6. customdried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-aa8d150336f2442bbe8ed61e251865ce
Source dataset
uspto-grants-1998_06
Patent number
US05760035

Linked notes

Loading…