Dehydration of fructose to 5-Hydroxymethylfurfural with ZrCl4; 5-Hydroxymethylfurfural
SyntheticPage 769
DOI:
10.1039/SP769
Submitted Nov 22, 2014, published Nov 24, 2014
Chemicals Used
D-Fructose
Zirconium Chloride
Nitromethane
Procedure
Solution containing D-Fructose (1 g, 5.55mmol) in nitromethane (10mL) was charged into a 50 mL flask, followed by the addition of ZrCl4 (0.129 g, 0.55mmol).The mixture was then heated at 1000C for 3 h, while stirred with a magnetic stirrer. Reaction mixture was cooled to rt and evaporated under reduced pressure to get crude mass, which was diluted with water (25 mL) and extracted with ethyl acetate (50 mLĂ—4).After drying on Na2SO4 extracts were concentrated on rotatory evaporator. Purification by column chromatography (80-20% ethyl acetate in petroleum ether as eluent) to gave 5-Hydroxymethylfurfural (0.52g, yellow oil, yield:73%).
Author's Comments
For time and temp optimization see ref.
Guard tube with fresh anhydrous calcium chloride was placed over water condenser.
Data
1H NMR (200 MHz, CDCl3):4.12 (bs, 1H), 4.66 (s, 2H), 6.49 (d, J=4Hz, 1H), 7.21 (d, J=4Hz, 1H), 9.49 (s, 1H).
Lead Reference
Supplementary Information
1H NMR (1 NMR.JPG)
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Keywords: alcohols, aldehydes, carbohydrates and sugars, Dehydration, elimination, heterocyclic compounds