tert-Butyl hydroperoxide → 2,2,6,6-Tetramethyl-1-(1-phenylethoxy)piperidin-4-one

Participants

Reaction Steps

A mixture of 40.0 grams (235 mmol) of 1-oxyl-2,2,6,6-tetramethylpiperidin-4-one, 60.5 grams (470 mmol) of 70% aqueous tert-butyl hydroperoxide, 3.0 grams of molybdenum trioxide, and 200 ml of ethylbenzene is heated at reflux for four hours. Water is collected in a Dean-Stark trap. Solids are removed by filtration, and the filtrate is concentrated under reduced pressure. Kugelrohr distillation of the crude product, followed by recrystallization from methanol, affords 42.8 grams (67% yield) of the title compound as a white solid melting at 77-80° C.

Provenance & Evidence