Abstract

A synthetic approach towards methyl protocatechuate via chemoselective ether cleavage of methyl vanillate without affecting the carboxylate group is disclosed utilizing a ternary reagent system consisting of aluminum triiodide, 1,3-diisopropylcarbodiimide and ethyl acetate. Ethyl acetate serves as a co-solvent and sacrificial ester. Methyl isovanillate, ethyl vanillate and methyl feruate were analogously demethylated to give methyl protocatechuate, ethyl protocatechuate and methyl caffeate, respectively, in fair to excellent yields.

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