Issue 4, 2014

One-pot formal synthesis of biorenewable terephthalic acid from methyl coumalate and methyl pyruvate

Abstract

Diverse functionalized aromatic compounds are constructed from captodative dienophiles with exclusive regioselectivity. 100% biorenewable dimethyl terephthalate (DMT) from methyl coumalate and methyl pyruvate is achieved in a one-pot, Diels–Alder/decarboxylation/elimination sequence in nearly quantitative yield. The DMT system is solvent-free and purification is accomplished through recrystallization. DMT hydrolysis reveals the co-monomer terephthalic acid (TPA) as a bio-based drop-in replacement for the polymer industry, avoiding harsh oxidation and petrochemicals.

Graphical abstract: One-pot formal synthesis of biorenewable terephthalic acid from methyl coumalate and methyl pyruvate

Supplementary files

Article information

Article type
Communication
Submitted
06 Dec 2013
Accepted
23 Jan 2014
First published
23 Jan 2014

Green Chem., 2014,16, 2111-2116

Author version available

One-pot formal synthesis of biorenewable terephthalic acid from methyl coumalate and methyl pyruvate

J. J. Lee and G. A. Kraus, Green Chem., 2014, 16, 2111 DOI: 10.1039/C3GC42487A

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