Hydrochloric Acid → 5-Chloromethylfurfural

To the same three-necked flask as in Example 1 were added 5 g (0.028 mole) of a commercially available D-(-)-fructose and two kinds of surface active agent, i.e., 62.2 mg (0.00028 mole) of sodium laurate and 90.2 mg (0.00028 mole) of tetrabutylammonium bromide. Then, 5 ml of water and 30 ml of carbon tetrachloride 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. After stirring was continued at room temperature for a further 2.5 hours, the lower carbon tetrachloride layer was separated from the upper aqueous layer. Thirty milli-liters of carbon tetrachloride and the above two surface active agents of the same amounts as above were then freshly added to the aqueous layer. After stirring was continued at room temperature for 2.5 hours, the lower carbon tetrachloride layer was again separated. This carbon tetrachloride extraction operation was repeated three times in total. All the carbon tetrachloride layers were combined and filtered through Celite. The filtrate was neutralized, dried and concentrated to obtain about 2.0 g of 5-chloromethylfurfural as a crude product.

1. stirringAfter stirring
2. customthe lower carbon tetrachloride layer was separated from the upper aqueous layer
3. additionThirty milli-liters of carbon tetrachloride and the above two surface active agents of the same amounts as above were then freshly added to the aqueous layer
4. stirringAfter stirring
5. waitwas continued at room temperature for 2.5 hours
6. customthe lower carbon tetrachloride layer was again separated
7. extractionThis carbon tetrachloride extraction operation
8. filtrationfiltered through Celite
9. customdried
10. concentrationconcentrated

ORD record

ord-5abbc913e5014abf951c4a73ec1a02fe

Source dataset

uspto-grants-1979_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04154744