Dimedone → 3-Chloro-5,5-dimethyl-2-cyclohexen-1-one

HRID 329697Notes

Reaction equation

HRID 329697 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:9][C:7](=O)[CH2:6][C:4](=[O:5])[CH2:3]1.C(Cl)(=O)C([Cl:14])=O>C(Cl)(Cl)Cl>[Cl:14][C:7]1[CH2:9][C:2]([CH3:10])([CH3:1])[CH2:3][C:4](=[O:5])[CH:6]=1

Participants

4

Reactant 2

HCID 31358DimedoneHCID 65578Oxalyl chloride

Product 1

HCID 1402433-Chloro-5,5-dimethyl-2-cyclohexen-1-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The title compound was prepared using the method of Clark and Heathcock. J. Org. Chem., 1976, 41, 636. To a suspension of dimedone (15.0 g, 107 mmol) in chloroform (40 ml) was added slowly oxalyl chloride (27.2 g, 214 mmol). The addition was accompanied by vigorous evolution of gas. After stirring at room temperature for 10 minutes, the slurry was refluxed for 20 minutes to give a yellow solution which was evaporated and distilled to give 15.7 g (92%) of chloroenone as a colorless liquid, bp 72° (5 mm). ##STR5##

Workup

  1. additionThe addition
  2. temperaturethe slurry was refluxed for 20 minutes
  3. customto give a yellow solution which
  4. customwas evaporated
  5. distillationdistilled
  6. customto give 15.7 g (92%) of chloroenone as a colorless liquid, bp 72° (5 mm)

Sources & evidence

ORD record
ord-7833946204f04538a62bdc11dfdfc943
Source dataset
uspto-grants-1990_01
Patent number
US04892884

Reaction notes

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