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

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Reaction Steps

A solution of 9.1 g (80 mmol) of 30% aqueous hydrogen peroxide is added dropwise, under nitrogen, over a 30-minute period to a mixture of 10.0 g (58.1 mmol) of 4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine, 17.8 g (64.0 mmol) of ferrous sulfate heptahydrate, and 100 ml of dimethyl sulfoxide which is initially at 23° C. The reaction temperature reaches 65° C. during the addition. After the peroxide is all added, the reaction mixture is stirred for 30 minutes. During this time, the temperature falls to 35° C. The reaction mixture is partitioned between methylene chloride (150 ml) and water (100 ml). The organic layer is dried over anhydrous magnesium sulfate and concentrated at reduced pressure to obtain a yellow liquid. Purification by flash chromatography on silica gel (10:1 heptane/ethyl acetate, then 4:1 heptane/ethyl acetate) affords 6.5 g (60% yield) of the title compound.

Provenance & Evidence