Health & Environmental Research Online (HERO)


Print Feedback Export to File
6837431 
Journal Article 
An innovative synthesis pathway to benzodioxanes: the peculiar reactivity of glycerol carbonate and catechol 
Tabanelli, T; Giliberti, C; Mazzoni, R; Cucciniello, R; Cavani, F 
2019 
Yes 
Green Chemistry
ISSN: 1463-9262
EISSN: 1463-9270 
v. 21 
no. 2 
329-338 
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. 
alkylation agents; carbonates; catalysts; catechol; dioxane; gas chromatography-mass spectrometry; glycerol; green chemistry; isomers; magnesium oxide; nuclear magnetic resonance spectroscopy; pharmaceutical industry; solvents 
OPPT REs
• OPPT_1,4-Dioxane_D. Exposure
     Total – title/abstract screening
          Supplemental Search
               Consumer Use