Water → Bis(1-cyclooctyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate

Participants

Reaction Conditions

Reaction Steps

A mixture of 75 g (156 mmol) of di-(2,2,6,6-tetramethylpiperidin-4-yl) sebacate, 1.3 g of molybdenum trioxide and 475 ml of cyclooctane is heated to 118° C. To this mixture is added 130 g (1.01 mol) of 70% aqueous tert-butyl hydroperoxide during a 5-hour period. The reaction mixture is maintained at reflux during the addition period, and water is collected in a Dean-Stark trap. The red reaction mixture is heated at reflux for 7 hours after the addition is complete to discharge the red color. The solids are removed by filtration and the filtrate is evaporated to give a yellow oil. Purification (Waters Prep 500A HPLC, 20:1 hexane:ethyl acetate) affords 78.7 g (68% yield) of the title compound as a colorless syrup.

Provenance & Evidence