tert-Butyl hydroperoxide → Tinuvin 123

Participants

Reaction Conditions

Reaction Steps

A mixture of 15.0 g (31.2 mmol) of di-(2,2,6,6-tetramethylpiperidin-4-yl) sebacate, 0.2 g of chromium (VI) oxide, and 120 ml of n-octane is heated to 115° C. To the above mixture is added 28.5 g (221 mmol) of 70% aqueous tert-butyl hydroperoxide over a 90-minute interval while the reaction mixture is heated at reflux. Water is collected in a Dean-Stark trap. The red mixture is heated at reflux for 3.25 hours after the addition is complete in order to discharge the color. The reaction mixture is passed through 150 g of silica gel with 2:1 heptane:ethyl acetate as the eluent. The organic solution is evaporated to obtain a yellow liquid which is purified (Waters 500A HPLC; silica gel; 20:1 hexane:ethyl acetate) to afford 15.3 g (67% yield) of the title compound. The product has the same LC retention time as the compound prepared in Example 31.

Provenance & Evidence