New oxidation products of 2,2,5,7,8‐pentamethyl‐6‐chromanol

Oxidation of the α‐tocopherol model compound 2,2,5,7,8‐pentamethyl‐6‐chromanol (1) byt‐butyl hydroperoxide in chloroform, to which an alcohol has been added, produces 5‐alkoxymethyl‐2,2,7,8‐tetramethyl‐6‐chromanol as the major product. In the present study,1 was oxidized byt‐butyl hydroperoxide in water‐saturated chloroform to determine whether water would influence product formation in the same way as alcohols. In addition to the usual products of oxidation such as 2‐(3‐hydroxy‐3‐methylbutyl)‐3,5,6‐trimethyl‐1,4‐benzoquinone (9), 5‐formyl‐2,2,7,8‐tetramethyl‐6‐chromanol (11), the spirodimer and spirotrimer of1, three new products have been identified−2,2,7,8‐tetramethyl‐5‐(2,2,5,7,8‐pentamethyl‐6‐chromanoxy)methyl‐6‐chromanol (4), 5‐hydroxymethyl‐2,2,7,8‐tetramethyl‐6‐chromanol (5) and 3‐hydroxymethyl‐2‐(3‐hydroxy‐3‐methylbutyl)‐5,6‐dimethyl‐1,4‐benzoquinone (7).