Hydrochloric Acid → 5-Chloromethylfurfural

To a three-necked flask equipped with a condenser and a stirrer were added 5 g (0.028 mole) of a commercially available D-(-)-fructose and a surface active agent, 82.3 mg (0.00028 mole) of lauryldimethylbetaine. Then, 5 ml of water and 30 ml of toluene were added thereto and the mixture was stirred. Thereafter, a molar excess of hydrogen chloride was passed through the mixture at room temperature for about 30 minutes with thorough stirring. After the reaction was continued at room temperature for a further 3 hours, the upper toluene layer was separated from the lower aqueous layer. Thirty milli-liters of toluene and the above surface active agent in the same amount as above were then freshly added to the aqueous layer. After the reaction was carried out at room temperature for 3 hours, the upper toluene layer was again separated. This toluene extraction operation was repeated three times in total. All the toluene layers were combined and filtered through Celite. The filtrate was neutralized with an aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate and concentrated. Thus, about 2.9 g of 5-chloromethylfurfural was obtained as a crude product.

1. customTo a three-necked flask equipped with a condenser and a stirrer
2. customthe upper toluene layer was separated from the lower aqueous layer
3. additionThirty milli-liters of toluene and the above surface active agent in the same amount as above were then freshly added to the aqueous layer
4. waitAfter the reaction was carried out at room temperature for 3 hours
5. customthe upper toluene layer was again separated
6. extractionThis toluene extraction operation
7. filtrationfiltered through Celite
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated

ORD-Eintrag

ord-24f5dae1dd124173b931c8e94bc0f81d

Quelldatensatz

uspto-grants-1979_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04154744