Hydrochloric Acid → 5-Chloromethylfurfural

Participants

Reaction Steps

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.

Provenance & Evidence