Efficient two directional syntheses of a homophthalate ester and novel resorcylate oligomers

Thermolysis of 6,6′-(2-oxopropane-1,3-diyl)bis(2,2-dimethyl-4H-1,3-dioxin-4-one) in the presence of methanol gave a triketo-ester which subsequently aromatized to provide a synthetically useful homophthalate ester. Enolate C-acylation in the presence of diethylzinc was used to synthesize other double diketo-dioxinones, which on cyclization, aromatization and dioxinone ring opening gave novel double resorcylate derivatives.