Hydrochloric Acid → 5-Chloromethylfurfural

Participants

Reaction Steps

To a three-necked flask equipped with a condenser and a stirrer were added 5 g (0.028 mole) of a commercially available D-(+)-glucose and two kinds of surface active agent, i.e., 97.6 mg (0.00028 mole) of sodium laurylbenzenesulfonate and 89.6 mg (0.00028 mole) of cetyltrimethylammonium chloride. 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 (about 13 g) was passed through the mixture at room temperature for about 25 minutes with thorough stirring, and then stirring was continued at 45° C. for a further 3 hours. After the supernatant toluene layer was separated from the reaction solution, 30 ml of toluene was freshly added to the residual aqueous layer. After the mixture was stirred at 45° C. for 2 hours, the upper toluene layer was again separated. This toluene extraction operation was repeated four 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 2.4 g (theoretical yield 4.01 g) of 5-chloromethylfurfural was obtained as a crude liquor of pale brown color.

Provenance & Evidence