A compound A (C₁₁H₁₄O₃) is insoluble in base and gives an isomeric compound B when heated strongly. Compound B gives a sodium salt when treated with NaOH.

Treatment of the sodium salt of B with dimethyl sulfate gives a new compound C (C₁₂H₁₆O₃) that is identical in all respects to a natural product elemicin. Ozonolysis of elemicin followed by oxidation gives the carboxylic acid D. Propose structures for compounds A, B, and C.

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H,CO. OCH3 -OCH3 CH,CO,H D