Sodium Chloride → 4-Benzoyloxy-1-(1'-methylcyclohexyloxy)-2,2,6,6-tetramethylpiperidine

HRID 1650033Notes

Reaction equation

HRID 1650033 reaction equation
C(OO)(C)(C)C.[Cl-].[Na+].[C:9]([O:17][CH:18]1[CH2:23][C:22]([CH3:25])([CH3:24])[N:21]([OH:26])[C:20]([CH3:28])([CH3:27])[CH2:19]1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH3:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>[Mo](=O)(=O)=O>[C:9]([O:17][CH:18]1[CH2:19][C:20]([CH3:28])([CH3:27])[N:21]([O:26][C:30]2([CH3:29])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[C:22]([CH3:24])([CH3:25])[CH2:23]1)(=[O:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6410tert-Butyl hydroperoxideHCID 7962Methylcyclohexane2×HCID 6881781-Hydroxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 197683284-Benzoyloxy-1-(1'-methylcyclohexyloxy)-2,2,6,6-tetramethylpiperidineYield 89%

Reagents, catalysts & solvents 1

HCID 14802Molybdenum trioxideCatalyst

Procedure

t-Butyl hydroperoxide (70%, 65.2 g, 507 mmol), methylcyclohexane (150 ml), and sodium chloride (10 g) are agitated in a separatory funnel. The organic layer is dried over magnesium sulfate. The t-butyl hydroperoxidemethylcyclohexane solution is mixed with 35.0 g (127 mmol) of 4-benzoyloxy-1-oxyl-2,2,6,6-tetramethylpiperidine, 2.0 g of molybdenum trioxide, and 50 ml of methylcyclohexane. The reaction mixture is heated at reflux for 5 hours, then cooled to room temperature, filtered, and concentrated at reduced pressure. The crude product is diluted with heptane and passed through a short column of silica gel with heptane as the eluent to afford, after evaporation of solvent, 42.4 g (89% yield) of a clear colorless oil.

Workup

  1. dry with materialThe organic layer is dried over magnesium sulfate
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux for 5 hours
  4. filtrationfiltered
  5. concentrationconcentrated at reduced pressure
  6. additionThe crude product is diluted with heptane
  7. customto afford

Sources & evidence

ORD record
ord-645c14cf23014f4bbc553f368f21f858
Source dataset
uspto-grants-1990_05
Patent number
US04921962

Reaction notes

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