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

HRID 1493525

Reaktionsgleichung

Reaktionsgleichung von HRID 1493525
[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])(C)C>[Mo](=O)(=O)=O.CCCCCCCC>[C:1]([O:9][CH:10]1[CH2:15][C:14]([CH3:17])([CH3:16])[N:13]([O:24][CH2:20][CH2:23][CH2:6][CH2:7][CH2:2][CH2:3][CH2:4][CH3:5])[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 2

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

Produkt 1

HCID 151699944-Benzoyloxy-1-octyloxy-2,2,6,6-tetramethylpiperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14802Molybdenum trioxideKatalysatorHCID 356OctaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 55.3 grams (0.2 mol) of 4-benzoyloxy-2,2,6,6-tetramethylpiperidine, 2.8 grams of molybdenum trioxide and 250 ml of n-octane is heated to 120° C. A solution of 90.2 grams (0.7 mol) of 70% aqueous tert-butyl hydroperoxide is added dropwise to the hot reaction mixture. Water is removed by azeotropic distillation and collected in a Dean-Stark trap. The reaction mixture is heated at reflux till the red color of the intermediate N-oxyl compound disappears. Solids are removed by filtration, and the filtrate is concentrated under vacuum to give an oil. Purification of the oil by flash chromatography on silica gel (100:3 heptane: ethyl acetate) affords 4-benzoyloxy-1-octyloxy-2,2,6,6-tetramethylpiperidine as a mixture of octyloxy isomers. Further elution of the chromatographic column with 50:3 heptane:ethyl acetate affords the title compound as a mixture of octanediyl isomers.

Aufarbeitung

  1. customWater is removed by azeotropic distillation
  2. customcollected in a Dean-Stark trap
  3. temperatureThe reaction mixture is heated
  4. temperatureat reflux till the red color of the intermediate N-oxyl compound
  5. customSolids are removed by filtration
  6. concentrationthe filtrate is concentrated under vacuum
  7. customto give an oil
  8. customPurification of the oil by flash chromatography on silica gel (100:3 heptane: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-3fb9a37cc3b047c498cccbbc2b2d7b7b
Quelldatensatz
uspto-grants-1991_06
Patentnummer
US05021577

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