Hydrochloric Acid → 5-Chloromethylfurfural

Five grams (0.028 mole) of a commercially available D-glucose was added to a three-necked flask equipped with a condenser and a stirrer, and dissolved in 5 ml of water. Thirty milli-liters of toluene was further added and the mixture was stirred. Thereafter, a molar excess of hydrogen chloride (about 12 g) was passed through the mixture at room temperature for 30 minutes with thorough stirring. Stirring was further continued at 45° C. for 5 hours. The reaction solution containing a small amount of humud was diluted with a little water and filtered through Celite while being washed with a small amount of toluene. The toluene layer was neutralized with an aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate and concentrated. Thus, about 1.0 g (theoretical yield 4.01 g) of 5-chloromethylfurfural was obtained as a crude product of pale brown color.

1. customequipped with a condenser and a stirrer
2. stirringStirring
3. additionThe reaction solution containing a small amount of humud
4. filtrationfiltered through Celite
5. washwhile being washed with a small amount of toluene
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated

ORD record

ord-46cd8b7fadca4381af872669abd4eece

Source dataset

uspto-grants-1979_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04154744