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Sustainable synthesis of 1,2,3,4-cyclohexanetetracarboxylate from sugar-derived carboxylic acids

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Abstract

Herein, we report a sustainable route for the synthesis of 1,2,3,4-cyclohexanetetracarboxylate from sugar-derived muconic acid and fumaric acid. The key Diels–Alder reaction constructed a cyclohexene framework substituted by four ester groups. The isolated yield of tetramethyl 5-cyclohexene-1,2,3,4-tetracarboxylate was up to 95.5% without any catalyst used. And the hydrogenation reaction of the cycloadduct was catalyzed by commercial RANEY® Ni at room temperature and nearly 100% yield of the cyclohexyl target products was obtained.

Graphical abstract: Sustainable synthesis of 1,2,3,4-cyclohexanetetracarboxylate from sugar-derived carboxylic acids

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Article information


Submitted
24 Mar 2020
Accepted
29 May 2020
First published
01 Jun 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Sustainable synthesis of 1,2,3,4-cyclohexanetetracarboxylate from sugar-derived carboxylic acids

R. Lu, H. Jiang, X. Si, X. Luo, F. Lu and J. Xu, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC02163F

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