Effect of alcohols on the oxidation of the vitamin E model compound, 2,2,5,7,8-pentamethyl-6-chromanol.

The vitamin E model compound, 2,2,5,7,8-pentamethyl-6-chromanol, has been oxidized with t-butyl hydroperoxide in chloroform in order to simulate in vivo oxidations due to lipid hydroperoxides. In the presence of a variety of alcohols, ranging from methanol to cholesterol, the corresponding 5-alkoxymethyl-2,2,7,8-tetramethyl-6-chromanols were formed in fair to good yield and were the major products in each reaction.