[OH:1][CH2:2][C:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11]O)[OH:10])O)O)=O.C(OS(C1C=CC=CC=1)(=O)=O)CCCCCCCCCCC.[Na].O.[ClH:37]>[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.C1(C)C=CC=CC=1>[Cl:37][CH2:11][C:9]1[O:10][C:3]([CH:2]=[O:1])=[CH:5][CH:7]=1
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 two kinds of surface active agent, i.e., 89.6 mg (0.00028 mole) of cetyltrimethylammonium chloride and 97.6 mg (0.00028 mole) of sodium laurylbenzenesulfonate. 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 15 g) was passed through the mixture at room temperature for about 40 minutes with thorough stirring. After stirring was continued at room temperature for a further 2.5 hours, the upper toluene layer was separated from the lower aqueous layer. Thirty milli-liters of toluene and the above two surface active agents in the same amounts as above were then freshly added to the aqueous layer. After the mixture was stirred at room temperature for 2.5 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 3.10 g (theoretical yield 4.01 g) of 5-chloromethylfurfural was obtained as a crude liquor of pale brown color.
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