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Upgrading of Levulinic Acid with Dimethylcarbonate as Solvent/Reagent

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Department of Molecular Sciences and Nanosystems, Centre for Sustainable Technology, Università Ca’ Foscari Venezia, Dorsoduro 2137, 30123 Venezia, Italy
Cite this: ACS Sustainable Chem. Eng. 2013, 1, 8, 989–994
Publication Date (Web):May 2, 2013
Copyright © 2013 American Chemical Society

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    The reactivity of the biobased chemical levulinic acid with dimethylcarbonate as a solvent/reagent under basic conditions is here described. The reaction yields methyl levulinate and dimethyl succinate, along with products that derive from methylation of the aliphatic chain and the dimethylketal of methyl levulinate. A degree of control over selectivity can be achieved by tuning the reaction conditions.

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    Spectral (1H NMR and MS) characterization data of all compounds. This material is available free of charge via the Internet at

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    10. Alexandre Démolis, Nadine Essayem, and Franck Rataboul . Synthesis and Applications of Alkyl Levulinates. ACS Sustainable Chemistry & Engineering 2014, 2 (6) , 1338-1352.
    11. Yuan Ji, Jessica Sweeney, Jillian Zoglio, and David J. Gorin . Catalytic Methyl Transfer from Dimethylcarbonate to Carboxylic Acids. The Journal of Organic Chemistry 2013, 78 (22) , 11606-11611.
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