tert-Butyl hydroperoxide → 4-Benzoyloxy-1-cumyloxy-2,2,6,6-tetramethylpiperidine

HRID 1650030

Reaction equation

HRID 1650030 reaction equation
[C:1]([O:9][CH:10]1[CH2:15][C:14]([CH3:17])([CH3:16])[NH:13][C:12]([CH3:19])([CH3:18])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([O:24]O)([CH3:23])([CH3:22])[CH3:21]>[Mo](=O)(=O)=O.C1(C(C)C)C=CC=CC=1>[C:1]([O:9][CH:10]1[CH2:15][C:14]([CH3:17])([CH3:16])[N:13]([O:24][C:20]([C:23]2[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=2)([CH3:22])[CH3:21])[C:12]([CH3:19])([CH3:18])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6410tert-Butyl hydroperoxideHCID 5799672,2,6,6-Tetramethyl-4-piperidyl benzoate

Product 1

HCID 198552694-Benzoyloxy-1-cumyloxy-2,2,6,6-tetramethylpiperidineYield 76%

Reagents, catalysts & solvents 2

HCID 14802Molybdenum trioxideCatalystHCID 7406CumeneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 10.1 g (38.6 mmol) of 4-benzoyloxy-2,2,6,6-tetramethylpiperidine, 15.6 g (155 mmol) of 90% aqueous tert-butyl hydroperoxide, 600 mg of molybdenum trioxide and 60 ml of cumene is heated at 95° C. for two hours. The catalyst is removed by filtration and the filtrate is then evaporated at reduced pressure. The residual red oil is chromatographed on silica gel to afford 5.8 g (38% yield) of a white powder, m.p. 105°-108° C.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe filtrate is then evaporated at reduced pressure
  3. customThe residual red oil is chromatographed on silica gel

Sources & evidence

ORD record
ord-2b7f0248b9274b6fa1e9907b4112fdc3
Source dataset
uspto-grants-1990_05
Patent number
US04921962

Linked notes

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