title: Efficient one-pot synthesis of 5-chloromethylfurfural (CMF) from carbohydrates in mild biphasic systems.
abstract: 5-Halomethylfurfurals can be considered as platform chemicals of high reactivity making them useful for the preparation of a variety of important compounds. In this study, a one-pot route for the conversion of carbohydrates into 5-chloromethylfurfural (CMF) in a simple and efficient (HCl-H3PO4/CHCl3) biphasic system has been investigated. Monosaccharides such as D-fructose, D-glucose and sorbose, disaccharides such as sucrose and cellobiose and polysaccharides such as cellulose were successfully converted into CMF in satisfactory yields under mild conditions. Our data shows that when using D-fructose the optimum yield of CMF was about 47%. This understanding allowed us to extent our work to biomaterials, such as wood powder and wood pulps with yields of CMF obtained being comparable to those seen with some of the enumerated mono and disaccharides. Overall, the proposed (HCl-H3PO4/CHCl3) optimized biphasic system provides a simple, mild, and cost-effective means to prepare CMF from renewable resources.
authors.affiliation: Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8005, USA.
authors.forename: Wenhua
authors.initials: W
authors.lastname: Gao
authors.forename: Yiqun
authors.initials: Y
authors.lastname: Li
authors.forename: Zhouyang
authors.initials: Z
authors.lastname: Xiang
authors.forename: Kefu
authors.initials: K
authors.lastname: Chen
authors.forename: Rendang
authors.initials: R
authors.lastname: Yang
authors.forename: Dimitris S
authors.initials: DS
authors.lastname: Argyropoulos
mesh_terms: D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D002482:Cellulose / Q000737:chemistry; D004187:Disaccharides / Q000737:chemistry; D005632:Fructose / Q000737:chemistry; D005662:Furaldehyde / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D009005:Monosaccharides; D013395:Sucrose / Q000737:chemistry
chemical_list: C545952:5-(chloromethyl)furfural; D002241:Carbohydrates; D004187:Disaccharides; D009005:Monosaccharides; D005632:Fructose; D013395:Sucrose; D002482:Cellulose; D005662:Furaldehyde; D005947:Glucose