Issue 2, 2019

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

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

Supplementary files

Article information

Article type
Paper
Submitted
04 Sep 2018
Accepted
11 Dec 2018
First published
17 Dec 2018

Green Chem., 2019,21, 329-338

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, 21, 329 DOI: 10.1039/C8GC02811G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements