tert-Butyl hydroperoxide → 1-Cyclohexyloxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

HRID 1493392

Reaktionsgleichung

Reaktionsgleichung von HRID 1493392
[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)(C)([CH3:22])[CH3:21].[CH2:26]1[CH2:31]CCC[CH2:27]1>[Mo](=O)(=O)=O>[C:1]([O:9][CH:10]1[CH2:15][C:14]([CH3:17])([CH3:16])[N:13]([O:24][CH:20]2[CH2:22][CH2:31][CH2:26][CH2:27][CH2:21]2)[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

Komponenten

5

Edukt 3

HCID 6410tert-Butyl hydroperoxideHCID 8078CyclohexaneHCID 5799672,2,6,6-Tetramethyl-4-piperidyl benzoate

Produkt 1

HCID 233720981-Cyclohexyloxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14802Molybdenum trioxideKatalysator

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

A mixture of 10.5 grams (40.2 mmol) of 4-benzoyloxy2,2,6,6 tetramethylpiperidine, 16.1 grams (160.8 mmol) of 90% tert-butyl hydroperoxide, 600 mg of molybdenum trioxide and 60 ml of cyclohexane is placed in a Fischer-Porter pressure bottle (under a nitrogen atmosphere in an oil bath. The bath temperature is gradually increased to 135° C. over a 2.25 hour period and then maintained at 135° C. for another 2.25 hours till the red color of the N-oxyl intermediate is discharged. Solids are removed by filtration. The cyclohexane solution is washed twice with water, washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to yield an oil. Purification of the oil by flash chromatography (silica gel; 100:3 heptane:ethyl acetate) affords 12.8 grams of the title compound.

Aufarbeitung

  1. customSolids are removed by filtration
  2. washThe cyclohexane solution is washed twice with water
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto yield an oil
  7. customPurification of the oil by flash chromatography (silica gel; 100:3 heptane:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-87f8d6d784324d63a350adfdba29f362
Quelldatensatz
uspto-grants-1991_06
Patentnummer
US05021481

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