1-Butanol → beta-D-glucopyranosyl nitromethane

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Reaction Steps

50 g of moisture-free D-glucose are dissolved in 200 ml dimethyl sulphoxide and 100 ml methanol. 100 ml nitromethane and a suspension of 30 g sodium methylate in 320 ml methanol are added to the latter and stirring takes place for 24 hours at room temperature. 250 ml n-butanol are added to the reaction mixture and stirred for 1 hour at 0° C. The latter is then filtered and the residue washed with 100 ml isopropanol and 100 ml diethyl ether. After drying, 71 g of a bright yellow powder are obtained. The latter is dissolved in 200 ml water and passed through a column with 100 g of cation exchanger (Aldrich, Amberlyst 15, strongly acid H+ form). The ion exchanger is washed with 500 ml water. The aqueous, red solution is concentrated to 100 ml and heated to 90 ° C. over 30 hours. 2 g of fine activated carbon are added to the hot solution, which is then stirred for 10 minutes, filtered through 5 g kieselguhr and rewashed with 200 ml water.

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