Methane → 5-Chloromethylfurfural

Participants

Reaction Conditions

Reaction Steps

A paste prepared from D-(−)fructose, water (1.2 molar equiv), and MgCl2.6H2O (1.0 molar equiv) was added to toluene with stirring at 75° C., followed by stirring for 30 min at the same temperature. Then conc. HCl (8.6 molar equiv) was added to this solution in 5 min and stirred for another 1 h at 75° C. After the solution was cooled to room temperature under continuous stirring, a small amount of water and active charcoal were added and the mixture was stirred again. The organic layer, separated after filtration, was washed with brine, dried over anhydrous Na2SO4 and concentrated. Purification by column chromatography afforded 5-(chloromethyl)-2-furancarboxaldehyde in 80% yield.

Provenance & Evidence