Water → HCID 21999132, compound

HRID 1375132Notes

Reaction equation

HRID 1375132 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, compound

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) in cyclohexane (6 ml) was added water (0.8 ml), ruthenium trichloride hydrate (1.3 mg) and 70% t-BuOOH (1.26 ml). The solution was stirred at room temperature for 6 hours, filtered through a pad of celite and poured into a solution of 10% Na2SO4. The solution was extracted with ethanol, washed with brine, dried with MgSO4 and distilled off under reduced pressure. The residue was purified by chromatography over silica gel to give 3-(12-acetoxydodecyl)-2,4,4-trimethyl-2-cyclohexen-1-one as a colorless oil (227 mg). TLC: (hexane-AcOEt: 3-7) Rf=0.68

Workup

  1. filtrationfiltered through a pad of celite
  2. additionpoured into a solution of 10% Na2SO4
  3. extractionThe solution was extracted with ethanol
  4. washwashed with brine
  5. dry with materialdried with MgSO4
  6. distillationdistilled off under reduced pressure
  7. customThe residue was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-b314d4b8fa55457e8bbaf450d0d433c5
Source dataset
uspto-grants-2007_01
Patent number
US07166642B1

Reaction notes

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