Hydrogen Peroxide → N-cyclohexyloxy-4-oxo-2,2,6,6-tetramethylpiperidine

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A solution of 20.1 g (0.295 mol) of 50% aqueous hydrogen peroxide is added over 6 hours at 60° C. to a mixture of 8.51 g (50.0 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperid-4-one, 0.70 g (2.5 mmol) of iron(II) sulfate heptahydrate, 0.3 ml (5 mmol) of methanesulfonic acid, 11 ml of cyclohexane, and 90 ml of methanol. Shortly after the addition is completed, the reaction mixture tests negative for hydrogen peroxide. The reaction mixture is concentrated to afford 4.4 g (35% yield) of the title compound, isolated as a yellow oil. Structure is confirmed by mass spectrometry and NMR analysis.

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