Dimethyl Sulfoxide → 1-Methoxy-2,2,6,6-tetramethyl-piperidin-4-ol

Participants

Reaction Steps

A solution of 17.9 g (64.4 mmol) of ferrous sulfate heptahydrate in 80 ml of water and a solution of 9.7 g (86 mmol) of 30% aqueous hydrogen peroxide are simultaneously added, under nitrogen, over a 90-minute interval to a mixture of 10.0 g (58.1 mmol) of 4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine and 100 ml of dimethyl sulfoxide which is initially at 23° C. The temperature increases to 29° C. during the peroxide addition. After the addition is complete, the reaction mixture is stirred for two hours. The mixture is extracted with methylene chloride (200 ml, then 100 ml), and the crude product is purified by flash chromatography on silica gel (10:1 heptane/ethyl acetate, then 5:1 heptane/ethyl acetate) to afford 6.9 g (63% yield) of the title compound.

Provenance & Evidence