Nitration of a-tocopherol acetate 1b yielded 5-nitromethyl-gamma-tocop
herol acetate 2b. The acetate 2b was converted to free phenol 2a by tr
ansesterification in methanol. Reduction of 2b by NaBH4 in ethyl aceta
te and methanol gave 5-(2-hydroxypropyl)-gamma-tocopherol 5a and 5-met
hoxymethyl-gamma-tocopherol 6 respectively.