2-Isopropylcyclohexan-1-ol → 2-Isopropylcyclohexan-1-one

HRID 434764Notes

Reaction equation

HRID 434764 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1C1C=CC=C[NH+]=1.[Cr](Cl)([O-])(=O)=O.[CH:23]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]1[OH:32])([CH3:25])[CH3:24]>ClCCl>[CH:23]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][C:27]1=[O:32])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 953312-Isopropylcyclohexan-1-olHCID 178526115HCID 178526115, compound

Product 1

HCID 704902-Isopropylcyclohexan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4.0 g. (13.7 mmole) of 2,2'-bipyridinium chlorochromate in 15 ml of dichloromethane is added, while stirring, 0.5 g. (3.5 mmole) of 2-isopropylcyclohexanol in 10 ml of dichloromethane. The resulting reaction mixture is stirred for 4 hours and then filtered through a Hirsch funnel packed with 2 cm of Celite®. The resulting clear filtrate is washed with 5% hydrochloric acid and 10% sodium carbonate, and dried over magnesium sulfate. The drying agent is then removed and the solvent evaporated to yield a colorless oil which is distilled via Kugelrohr to yield pure 2-isopropylcyclohexanone in a typical yield of 0.425 g. which is 86% of theoretical yield.

Workup

  1. additionTo a suspension of 4.0 g
  2. customThe resulting reaction mixture
  3. stirringis stirred for 4 hours
  4. filtrationfiltered through a Hirsch funnel
  5. washThe resulting clear filtrate is washed with 5% hydrochloric acid and 10% sodium carbonate
  6. dry with materialdried over magnesium sulfate
  7. customThe drying agent is then removed
  8. customthe solvent evaporated
  9. customto yield a colorless oil which
  10. distillationis distilled via Kugelrohr

Sources & evidence

ORD record
ord-202a73537e6b474f91ffe9d816766776
Source dataset
uspto-grants-1983_08
Patent number
US04399281

Reaction notes

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