Sodium Hydroxide → D-(-)-Fructose

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This Example details the synthesis of fructose hydroxypropyl trimethylammonium chloride. A round bottom 250 ml flask was fitted with a mechanical stirrer. Into the flask was charged 1 M sodium hydroxide (55.5 ml, 55.5 mmol), Cornsweet (10 g, 55.5 mmol) and 3-chloro-2-hydroxypropyl trimethylammonium chloride (15 ml, 55.5 mmol). Cornsweet is obtained from the Archer Daniels Midland Corporation as a 100% fructose material. The 3-chloro-2-hydroxypropyl trimethyl ammonium chloride was sourced from Aldrich Chemical Company as a 60% active material in water. It is also available as Quat® 188 from the Dow Chemical Company. The reactants were stirred at room temperature for 18 hours. Water was removed under reduced pressure at 50° C. to give a heterogeneous colorless syrup. Filtration through glass wool afforded fructose hydroxypropyl trimethylammonium chloride as a homogeneous clear and colorless syrup: m/z (ESI; M+–Cl−) 296; HPLC (Column: YMC-ODS-AQ, S5, 120A, 4.6×250 mm; Flow: 1 ml/min isocratic, 100% water; Detector: RI; Temperature: 35° C.) tr 3.16 min (Cornsweet-tr 3.17 min; CHPTMAC-tr 3.39 min).

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