Molecules 2013, 18(7), 7675-7685; doi:10.3390/molecules18077675
Communication

Efficient One-Pot Synthesis of 5-Chloromethylfurfural (CMF) from Carbohydrates in Mild Biphasic Systems

1 Departments of Chemistry and Forest Biomaterials, North Carolina State University, Raleigh, NC 27695-8005, USA 2 State Key Laboratory Pulp and Paper Engineering, South China University of Technology, Guangzhou 510460, China 3 Department of Chemistry, Jinan University, Guangzhou 510632, China 4 Center of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, P.O. Box 80203, Jeddah 21589, Saudi Arabia
* Author to whom correspondence should be addressed.
Received: 22 May 2013; in revised form: 24 June 2013 / Accepted: 25 June 2013 / Published: 2 July 2013
(This article belongs to the Special Issue Heterogeneous Catalysis)
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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.
Keywords: 5-chloromethylfurfural; carbohydrates; biphasic system

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    Correction (PDF, 180 KB)

    A correction was published on 22 January 2014 http://www.mdpi.com/1420-3049/19/1/1370 (PDF, 180 KB) The authors would like to make corrections of some errors and omissions in the Introduction section.

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MDPI and ACS Style

Gao, W.; Li, Y.; Xiang, Z.; Chen, K.; Yang, R.; Argyropoulos, D.S. Efficient One-Pot Synthesis of 5-Chloromethylfurfural (CMF) from Carbohydrates in Mild Biphasic Systems. Molecules 2013, 18, 7675-7685.

AMA Style

Gao W, Li Y, Xiang Z, Chen K, Yang R, Argyropoulos DS. Efficient One-Pot Synthesis of 5-Chloromethylfurfural (CMF) from Carbohydrates in Mild Biphasic Systems. Molecules. 2013; 18(7):7675-7685.

Chicago/Turabian Style

Gao, Wenhua; Li, Yiqun; Xiang, Zhouyang; Chen, Kefu; Yang, Rendang; Argyropoulos, Dimitris S. 2013. "Efficient One-Pot Synthesis of 5-Chloromethylfurfural (CMF) from Carbohydrates in Mild Biphasic Systems." Molecules 18, no. 7: 7675-7685.

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