Hydrogen Peroxide → 1-Cyclohexyloxy-2,2,6,6-tetramethyl-piperidin-4-ol

HRID 133658

Reaktionsgleichung

CS(O)(=O)=O.[OH:6][N:7]1[C:12]([CH3:14])([CH3:13])[CH2:11][CH:10]([OH:15])[CH2:9][C:8]1([CH3:17])[CH3:16].[C:18](#N)[CH3:19].OO>O.O.O.O.O.S([O-])([O-])(=O)=O.C([NH3+])C[NH3+].[Fe+2].S([O-])([O-])(=O)=O.C1CCCCC1>[CH:19]1([O:6][N:7]2[C:12]([CH3:13])([CH3:14])[CH2:11][CH:10]([OH:15])[CH2:9][C:8]2([CH3:17])[CH3:16])[CH2:18][CH2:10][CH2:9][CH2:8][CH2:16]1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

A solution of 0.404 g (1.1 mmol) of iron(II) ethylenediammonium sulfate tetrahydrate and 0.237 g (2.5 mmol) of methanesulfonic acid in 2 ml of water is added to a mixture of 5.00 g (29.0 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidin-4-ol, 38 ml of acetonitrile, and 24 ml of cyclohexane. The reaction mixture is heated to 50° C. A solution of 8.0 g (118 mmol) of 50% aqueous hydrogen peroxide is added to the reaction mixture dropwise over 4 hours while the temperature is brought to and maintained at reflux. After the peroxide is added, the reaction mixture is allowed to cool slowly to room temperature. The reaction mixture is stirred overnight at ambient temperature. The lower layer is discarded, and the organic layer is concentrated and purified by flash chromatography to afford 3.9 g (53% yield) of the title compound, a yellow solid. GC assay is greater than 99%.

Aufarbeitung

temperaturemaintained
temperatureat reflux
temperatureto cool slowly to room temperature
concentrationthe organic layer is concentrated
custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag: ord-66f1bd7a3d27410ab1669a7fd5e30273
Quelldatensatz: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07390904B2

Verknüpfte Notizen

Wird geladen…