[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]=1To a three-necked flask equipped with a condenser and a stirrer were added 2.5 g (0.014 mole) of a commercially available L-(-)-sorbose and two kinds of surface active agent, i.e., 47.1 mg (0.00014 mole) of cetyltrimethylammonium chloride and 51.3 mg (0.00014 mole) of sodium laurylbenzenesulfonate. Then, 2.5 ml of water and 15 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, and the mixture was stirred at room temperature for a further 2.5 hours. The reaction solution was filtered through Celite while being washed with a small amount of a water-toluene mixture. The toluene layer was neutralized, dried and concentrated to obtain about 1.0 g (theoretical yield 2.0 g) of 5-chloromethylfurfural as a crude product.
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