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

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Reaction Steps

A solution of 8.6 g (76 mmol) of 30% aqueous hydrogen peroxide is added dropwise, under nitrogen, over a 35-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 200 ml of dimethyl sulfoxide which is initially at 25° C. A water bath is used to keep the reaction temperature from exceeding 33° C. during the peroxide addition. The reaction mixture is then stirred for 25 minutes and partitioned between methylene chloride (200 ml) and water (100 ml). The aqueous layer is extracted with methylene chloride (100 ml). The combined organic layers are dried over anhydrous magnesium sulfate and concentrated at reduced pressure. The crude product is purified by flash chromatography on silica gel (10:1 heptane/ethyl acetate, then 4:1 heptane/ethyl acetate) to afford 8.6 g (79% yield) of the title compound.

Provenance & Evidence