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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence