COUMARINS FROM ORCINOL DERIVATIVES: CONDENSATION OF ORCACETOPHENONE MONOMETHYL ETHER WITH ETHYL ACETATE, ETHYL PROPIONATE AND ETHYL BUTYRATE, AND MOLECULAR REARRANGEMENT OF ORCACETOPHENONE DIACETATE AND DIBENZOATE, IN PRESENCE OF METALLIC SODIUM

Orcacetophcnone monomethyl ether has been condensed with ethyl acetate, ethyl propionate and ethyl butyrate in presence of metallic sodium.; instead of the expected \(\beta\)-diketones other products are obtained to which the structures of 4-hydroxy-7-methoxy-4 :5-dimethyl-, -3 :4:5-trimethyl-, and -3-ethyl-4 :5-dimethyl-3 :4-dihydrocoumarin respectively, have been tentatively assigned. Molecular rearrangement of orcacetophenone diacetate in presence of metallic sodium gives 7-hydroxy-4-acetome­thyl-5-methylconmarin instead of the isomeric chromone. The formation of coumarin derivatives in the above reactions has not been observed before. Similar rearrangement of orcacetophenone dibenzoate gives the expected 7-hydroxy-5-methylflavone.