17736-66-2Relevant 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.
Aromatic ethers and process for producing aromatic ethers
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Page 17, (2010/02/08)
According to a production process, aromatic ethers are producible by reacting phenols with an oxirane compound with use of an anion exchange resin as a catalyst. According to another production process, aromatic ethers having an alcoholic hydroxyl group are producible by a crystallization-purification step of using a solvent having a solubility parameter ranging from 7.5 to 12.5 for purification by crystallization. Further, according to still another production process, producible are aromatic ethers having an alcoholic hydroxyl group, wherein the content of a metal in the aromatic ethers is less than 100 ppm by mass, and the content of a halogen element in the aromatic ethers is less than 100 ppm by mass.
