Water → HCID 21999132, compound

HRID 1976756Notes

Reaction equation

HRID 1976756 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[C:22]([CH3:24])([CH3:23])[CH2:21][CH2:20][CH2:19][C:18]=1[CH3:25])(=[O:3])[CH3:2].O.C([O:31]O)(C)(C)C>C1CCCCC1.O.[Ru](Cl)(Cl)Cl>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[C:22]([CH3:24])([CH3:23])[CH2:21][CH2:20][C:19](=[O:31])[C:18]=1[CH3:25])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 6410tert-Butyl hydroperoxideHCID 21999134HCID 21999134, compound

Product 1

HCID 21999132HCID 21999132, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 8078CyclohexaneSolvent

Procedure

To a solution of 1-(12-acetoxydodecyl)-2,6,6-trimethyl-1-cyclohexene (321 mg, 0.92 mmol, 1 eq.) in cyclohexane (6 ml) was added water (0.8 ml), ruthenium trichloride hydrate (0.7% mol, 1.3 mg) and 70% t-BuOOH (1.26 ml, 10 eq.). The solution was stirred at room temperature for 6 hours, filtered through a pad of celite and poured into a solution of 10% Na2SO3. The solution was extracted with ether, washed with brine, dried with MgSO4 and concentrated in vacuo. The residue was purified by chromatography over silica gel, eluting with hexane-AcOEt (95-15 to 90-10) to give 3-(12-acetoxydodecyl)-2,4,4-trimethyl-2-cyclohexen-1-one as a colorless oil (227 mg, 53%).

Workup

  1. filtrationfiltered through a pad of celite
  2. additionpoured into a solution of 10% Na2SO3
  3. extractionThe solution was extracted with ether
  4. washwashed with brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography over silica gel
  8. washeluting with hexane-AcOEt (95-15 to 90-10)

Sources & evidence

ORD record
ord-61a170cbda284d81bb8baaa92c2f066b
Source dataset
uspto-grants-2001_05
Patent number
US06228893B1

Reaction notes

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