Abstract Via a synthetic sequence consisting of PPA-mediated Friedel− Crafts acylation of veratrol (8), Clemmensen reduction, demethylation with TMSI, Williamson ether synthesis employing 3-chloro-2-(chloromethyl) prop-1-ene and in-situ ruthenium tetroxide oxidation, numerous substituted benzo [b][1, 4] dioxepinones 15− 27 and 2, 3-dihydro-1H-5, 9- dioxacyclohepta [f] indenones 7, 13 and 14 were prepared to study their odor− structure ...