Methane → 5-Chloromethylfurfural

Temperature

75 °C

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.

1. stirringby stirring for 30 min at the same temperature
2. stirringstirred for another 1 h at 75° C
3. temperatureAfter the solution was cooled to room temperature under continuous stirring
4. stirringthe mixture was stirred again
5. customThe organic layer, separated
6. filtrationafter filtration
7. washwas washed with brine
8. dry with materialdried over anhydrous Na2SO4
9. concentrationconcentrated
10. customPurification by column chromatography

ORD record

ord-e7aa1cc24a1e44e0982c6c5b45a3421e

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07060678B2