Potassium Iodide → 2-Cyclohexenone, 5,5-dimethyl-

HRID 867084Notes

Reaction equation

HRID 867084 reaction equation
Cl[C:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4](=[O:10])[CH:3]=1.[I-].[K+]>CO.[Zn]>[CH3:8][C:6]1([CH3:9])[CH2:5][C:4](=[O:10])[CH:3]=[CH:2][CH2:7]1

Participants

5

Reactant 2

HCID 4875Potassium IodideHCID 1402433-Chloro-5,5-dimethyl-2-cyclohexen-1-one

Product 1

HCID 1383222-Cyclohexenone, 5,5-dimethyl-

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Activated zinc dust (15.0 g) was added to a stirred solution of 3-chloro-5,5-dimethylcyclohex-2-enone (9.0 g) and potassium iodide (7.5 g) in methanol (50 ml). After stirring for a period of 18 hours the mixture was filtered and the filtrate concentrated by evaporation under reduced pressure. The residue was mixed with dilute (8% w/v) hydrochloric acid and extracted with diethyl ether (2 × 100 ml). The combined ethereal extracts were washed with water and dried over anhydrous magnesium sulphate. After removal of the ether by evaporation under reduced pressure the residual oil was purified by distillation. 5,5-Dimethylcyclohex-2-enone was obtained as a pale yellow oil, b.p. 75° C./17 mm Hg.

Workup

  1. filtrationwas filtered
  2. concentrationthe filtrate concentrated by evaporation under reduced pressure
  3. additionThe residue was mixed
  4. additionwith dilute (8% w/v) hydrochloric acid
  5. extractionextracted with diethyl ether (2 × 100 ml)
  6. washThe combined ethereal extracts were washed with water
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customAfter removal of the ether
  9. customby evaporation under reduced pressure the residual oil
  10. distillationwas purified by distillation

Sources & evidence

ORD record
ord-ed4bcaa9561f4a89969a56d4bc50453d
Source dataset
uspto-grants-1978_07
Patent number
US04102896

Reaction notes

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