Mechanism of the dehydration of D-fructose to 5-hydroxymethylfurfural in dimethyl sulfoxide at 150 degrees C: an NMR study.
The anomeric composition of d-fructose in dimethyl sulfoxide changes when the solution is heated from room temperature to 150 degrees C, with a small increase in the alpha-furanose form at the expense of the beta-pyranose tautomer. Additionally, a small amount of alpha-pyranose form was also observed at 150 degrees C. A mechanism is proposed for the dehydration of D-fructose to 5-hydroxymethylfurfural in DMSO at 150 degrees C, where the solvent acts as the catalyst. A key intermediate in the reaction was identified as (4R,5R)-4-hydroxy-5-hydroxymethyl-4,5-dihydrofuran-2-carbaldehyde by using (1)H and (13)C NMR spectra of the sample during the reaction.
Amarasekara
Ananda S
AS
Department of Chemistry, Prairie View A&M University, Prairie View, TX 77446, USA. asamarasekara@pvamu.edu
Williams
LaToya D
LD
Ebede
Chidinma C
CC
D004121:Dimethyl Sulfoxide / Q000737:chemistry*; D005632:Fructose / Q000737:chemistry*; D005662:Furaldehyde / Q000031:analogs & derivatives* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013696:Temperature
D005632:Fructose; C008046:5-hydroxymethylfurfural; D005662:Furaldehyde; D004121:Dimethyl Sulfoxide