30067-20-0Relevant academic research and scientific papers
An innovative synthesis pathway to benzodioxanes: The peculiar reactivity of glycerol carbonate and catechol
Tabanelli,Giliberti,Mazzoni,Cucciniello,Cavani
, p. 329 - 338 (2019/01/28)
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.
PROCESS FOR OBTAINING PHENOLIC DERIVATIVES BY USING GLYCEROL CARBONATE
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Page/Page column 19; 20, (2018/10/19)
It is disclosed a process for obtaining phenolic derivatives with high industrial interest in the pharmaceutical industry by using glycerol carbonate. Specifically, the process provides for a phenol substituted in position 2 to react with glycerol carbonate in the presence of a basic catalyst capable of activating the substituted phenol. The reaction can be carried out in the presence of a homogeneous catalyst or a heterogeneous catalyst, ensuring in any case good selectivity and high yields towards the desired product.
