Hydrogen Peroxide → 1-(2-Hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-one

HRID 1276646Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1276646
CC(=NC1C=CC=CC=1)C(=NC1C=CC=CC=1)C.[H][H].[OH:21][N:22]1[C:27]([CH3:29])([CH3:28])[CH2:26][C:25](=[O:30])[CH2:24][C:23]1([CH3:32])[CH3:31].OO.N=O.[C:37]([OH:41])([CH3:40])([CH3:39])[CH3:38]>>[OH:41][C:37]([CH3:40])([CH3:39])[CH2:38][O:21][N:22]1[C:27]([CH3:28])([CH3:29])[CH2:26][C:25](=[O:30])[CH2:24][C:23]1([CH3:32])[CH3:31]

Komponenten

7

Edukt 6

HCID 784Hydrogen PeroxideHCID 945NitroxylHCID 6386tert-Butanol2×HCID 986421-Hydroxy-2,2,6,6-tetramethyl-4-oxopiperidineHCID 2210342,3-Dimethyl-1,4-diphenyl-1,4-diazabuta-1,3-dienHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 218850571-(2-Hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-one

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a mixture of 0.994 g (5 mmol) of ferrous chloride tetrahydrate and 150 mL of tert-butyl alcohol at 35° C. are added, sequentially, 1.18 g (5.0 mmol) of N,N'-(1,2-dimethyl1,2-ethanediylidene)bis(benzenamine), where in formula IV, X is hydrogen, and 17.0 g (100 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidin-4-one. A solution of 47.5 g (700 mmol) of 50% aqueous hydrogen peroxide mixed with 60 mL of tert-butyl alcohol is added over eight hours at 35-40° C. to the above mixture. The reaction is stirred an additional 16 hours at 40° C. Analysis by gas chromatography shows less than 4% starting nitroxyl present. Solids are removed by filtration, and the filtrate is reacted with aqueous sodium sulfite to decompose excess peroxide. The reaction mixture is thoroughly extracted with ethyl acetate to afford, after concentration, 21.4 g of crude product containing greater than 93% of the title compound as based on gas chromatography.

Aufarbeitung

  1. additionare added
  2. additionis added over eight hours at 35-40° C. to the above mixture
  3. customSolids are removed by filtration
  4. customthe filtrate is reacted with aqueous sodium sulfite
  5. extractionThe reaction mixture is thoroughly extracted with ethyl acetate
  6. customto afford
  7. concentrationafter concentration, 21.4 g of crude product
  8. additioncontaining greater than 93% of the title compound

Quellen und Nachweise

ORD-Eintrag
ord-770a9260ce0d4bcabd3f2001ccb69bf4
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06166212

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