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An innovative synthesis pathway to benzodioxanes: the peculiar reactivity of glycerol carbonate and catechol

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Abstract

A peculiar reactivity of glycerol carbonate (GlyC) as an innovative and highly reactive alkylating agent for phenolic compounds is investigated in this article. In particular, 2-hydroxymethyl-1,4-benzodioxane (HMB), a key intermediate for the pharmaceutical industry, has been selectively synthesized by the reaction of a slight excess of GlyC with catechol in the presence of a basic catalyst (NaOCH3, Na-mordenite, MgO), without requiring a reaction solvent. Both reagents have been quantitatively converted in just one hour at 170 °C with a HMB yield, up to 88%, in the presence of a homogeneous basic catalyst (NaOCH3). Notably, the main side product, the HMB isomer, may be an interesting intermediate for the synthesis of calone analogues, which are important scaffolds used in fragrances. A detailed mechanistic study, supported by kinetics, GC-MS, and HMBC NMR characterization, is also reported. Accordingly, this paper describes a completely innovative and greener synthesis pathway to benzodioxanes.

Graphical abstract: An innovative synthesis pathway to benzodioxanes: the peculiar reactivity of glycerol carbonate and catechol

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Publication details

The article was received on 04 Sep 2018, accepted on 11 Dec 2018 and first published on 17 Dec 2018


Article type: Paper
DOI: 10.1039/C8GC02811G
Citation: Green Chem., 2019, Advance Article
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    An innovative synthesis pathway to benzodioxanes: the peculiar reactivity of glycerol carbonate and catechol

    T. Tabanelli, C. Giliberti, R. Mazzoni, R. Cucciniello and F. Cavani, Green Chem., 2019, Advance Article , DOI: 10.1039/C8GC02811G

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