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. 2017 Jan 10;10(1):53-57.
doi: 10.1002/cssc.201601382. Epub 2016 Dec 22.

One-Pot Preparation of Dimethyl Isosorbide from d-Sorbitol via Dimethyl Carbonate Chemistry

F Aricò  1 , A S Aldoshin  1 , P Tundo  1
Affiliations

One-Pot Preparation of Dimethyl Isosorbide from d-Sorbitol via Dimethyl Carbonate Chemistry

F Aricò et al. ChemSusChem. .

Abstract

Direct synthesis of dimethyl isosorbide (DMI) from d-sorbitol via dimethyl carbonate (DMC) chemistry is herein first reported. High yield of DMI was achieved using the nitrogen superbase 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as catalyst and performing the reaction in a stainless steel autoclave by increasing the temperature from 90 to 200 °C. In this procedure, DMC features its full capacity acting in the different steps of the process as carboxymethylating, leaving-group (cyclization), and methylating agent; DMC is also employed as the reaction media.

Keywords: cyclic sugar; cyclization; dimethyl carbonate; isosorbide; methylation.

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