Hydrogen Peroxide → 1-Cyclohexyloxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

HRID 133647

Reaktionsgleichung

Reaktionsgleichung von HRID 133647
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([O:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][C:3]1([CH3:20])[CH3:19].C(#N)C.[CH2:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.OO>O>[CH:24]1([O:1][N:2]2[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([O:10][C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:4][C:3]2([CH3:20])[CH3:19])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Komponenten

6

Edukt 4

HCID 784Hydrogen PeroxideHCID 6342AcetonitrileHCID 8078CyclohexaneHCID 6881781-Hydroxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

Produkt 1

HCID 233720981-Cyclohexyloxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidineAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
56 °C

Versuchsvorschrift

A solution of 0.097 g (0.359 mmol) of ferric chloride hexahydrate in 2 ml of water is added to a mixture of 5.00 g (18.1 mmol) of 1-oxyl-4-benzoyloxy-2,2,6,6-tetramethylpiperidine, 28 ml of acetonitrile, and 19 ml of cyclohexane. The mixture is heated to 56° C. A solution of 4.70 g (69 mmol) of 50% aqueous hydrogen peroxide is added dropwise over 2.25 hours to the reaction mixture while the temperature is brought to and maintained at reflux. After the peroxide is added, the mixture is heated at reflux for 45 minutes. Work-up and purification according to the procedure of Example 5 afford 5.47 g (84% yield) of the title compound, a pale yellow syrup. GC assay is 100%.

Aufarbeitung

  1. temperaturemaintained
  2. temperatureat reflux
  3. temperaturethe mixture is heated
  4. temperatureat reflux for 45 minutes
  5. customWork-up and purification

Quellen und Nachweise

ORD-Eintrag
ord-08c14529a5624a229bb297bff01f9af8
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390904B2

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