The 0, O-dibenzyl ether of the 3, 4-catechol derivative of propranolol (1 1) was prepared to determine whether the catechol is a product of metabolic hydroxylation. 4-(Allyloxy)-1, 2- naphthoquinone (5) was reduced with sodium dithionite and alkylated with benzyl chloride to produce ether 7. Osmium tetroxide oxidation of 7 afforded glycol 8. Subsequent monotosylation, oxirane formation with KOH, and opening with isopropylamine afforded ...
