MATTHEW HARTLE¹, PETER SYMONS¹, SHRI HEGDE², PIERRE-GEORGES ECHEVERRIA^3*
*Corresponding author
1. Electrosynthesis Company, NY, USA
2. Pennakem, Memphis, TN, USA
3. Minakem Recherche, Beuvry la Forêt, France

Abstract

This article showcases the design of an electrochemical dimethoxylation reaction of bio-based furan. This transformation provides a key synthetic platform for the preparation of a broad range of compounds. 

The reaction parameters were first optimized under batch mode and then were successfully transposed to a continuous flow process.

INTRODUCTION

2,5-Dimethoxydihydrofuran motif is a versatile structure allowing the access to a wide variety of valuable chemicals (Figure 1). For example, starting from such dimethoxylated compound, several molecules of high interest for the food industry, such as furaneol (also called strawberry furanone) or maltol (flavor enhancer) (1, 2), can be prepared. Furthermore, this linchpin molecule provides a convenient means to access to a broad selection of agrochemical precursors such as methyl levulinate (3, 4), pyridazine (5) or 4-hydroxycyclopentenone (6), as well as tropane alkaloids known to exhibit interesting pharmacological properties (anticholinergics or stimulants) (7).

In recent decades, great efforts have been devoted to the development of more eco-friendly and sustainable chemical processes, either by using bio-based materials, by avoiding hazardous chemicals and/or by reducing the generation of waste. This endeavor, called “Green Chemistry” (8, 9), has recently benefited from the resurgence of electrochemistry, which is inherently a very “green” technique based on the use of the simplest possible reagents, elect ...