4-Chlorophenol → 1-Chloro-4-(3-chloropropoxy)benzene

HRID 1704098Notes

Reaction equation

HRID 1704098 reaction equation
Br[CH2:2][CH2:3][CH2:4][Cl:5].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:5][CH2:4][CH2:3][CH2:2][O:13][C:10]1[CH:11]=[CH:12][C:7]([Cl:6])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 126856101-Chloro-4-(3-chloropropoxy)benzeneYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 157 g of 3-bromo-1-chloropropane, 129 g of p-chlorophenol and 165 g of potassium carbonate in 1 liter of acetone is refluxed for 3 days. The mixture is cooled, filtered and the filtrate concentrated under reduced pressure. The residue is distilled to give 184 g of product as an oil, bp 107°-116° C. at 0.5mm.

Workup

  1. temperatureis refluxed for 3 days
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. distillationThe residue is distilled

Sources & evidence

ORD record
ord-44478036caa245dbb5760e9c3a7c950b
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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