In the face of depleting fossil fuels that primarily drive the chemical industry, carbohydrates could be an alternative feedstock for commodity chemicals like terephthalic acid.  The 2-pyrone methyl coumalate, ultimately accessible from glucose, is a versatile platform for diverse functionalized aromatics.  100% biorenewable dimethyl terephthalate (DMT) is achieved through a one-pot Diels-Alder/decarboxylation/elimination sequence in nearly quantitative yield from methyl coumalate and methyl pyruvate derivatives.  Advantageously, no solvent or catalysts are required and the product is purified by recrystallization.  A simple hydrolysis can produce completely bio-based terephthalic acid as a drop-in replacement for the polymer industry to avoid harsh oxidation and petrochemicals.

Formal synthesis of 100% biorenewable terephthalic acid

248th National Meeting (2014)

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