1-Chloro-4-(4-chlorophenyl)butan-2-ol → 1-Chloro-4-(4-chlorophenyl)butan-2-one

HRID 354589Notes

Reaction equation

HRID 354589 reaction equation
[Cl:1][CH2:2][CH:3]([OH:13])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O.O>[Cl:1][CH2:2][C:3](=[O:13])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 124320331-Chloro-4-(4-chlorophenyl)butan-2-olHCID 131709961Jones' reagent

Product 1

HCID 128164651-Chloro-4-(4-chlorophenyl)butan-2-oneYield 97.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 1-chloro-4-(4-chlorophenyl)-2-butanol (125 g) in acetone (200 ml) at 0° C. was treated with 570 ml of Jones reagent (from sodium dichromate dihydrate (100 g), concentrated sulfuric acid (136 g) and water to 500 ml) and stirred overnight at room temperature. The resulting solution was diluted with water (200 ml), extracted with ether (3×300 ml) and the extracts washed with water, aqueous sodium bicarbonate, and dried (MgSO4). Evaporation of the ether gave 121 g of 1-chloro-4-(4-chlorophenyl)-2-butanone. The analytical sample from hexane had m.p. 65°-67° C.

Workup

  1. extractionextracted with ether (3×300 ml)
  2. washthe extracts washed with water, aqueous sodium bicarbonate
  3. dry with materialdried (MgSO4)
  4. customEvaporation of the ether

Sources & evidence

ORD record
ord-864bb812126e4cc4b9f770d7b72f7ab3
Source dataset
uspto-grants-1983_03
Patent number
US04375474

Reaction notes

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