1-Butanol → (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

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Reaction Conditions

Reaction Steps

A maleic acid ester of an APG is prepared as follows. To a 1 L erlenmeyer flask, containing a magnetic stir bar, 185.1 g anhydrous n-butanol (Aldrich, 99.8%), 36.1 g n-octanol (Aldrich, 99+%), and 2.0 g deionized water are added. To the stirred mixture, 0.184 g (100 mL) of concentrated sulfuric acid (J. T. Baker, 96.6%) is added using a 1 mL glass syringe. This mixture is added to a 500 mL three necked round bottom flask containing 50.0 g of anhydrous α-D-glucose (Aldrich, 96%) and a concave magnetic stir bar. The flask is fitted with a thermocouple probe, a dry air intake, and a 25 mL Barrett receiver on which two glass condensers are mounted, which are connected to a gas bubbler. The condensate collection side of the Barrett receiver is filled with n-heptane, and the gas flow-through side is wrapped in cotton wool for the purpose of insulation. Dry air, passed over a 10 inch column filled with dry molecular sieves and Drierite, is passed through the liquid phase in the round bottom flask. The flask is heated for 4 hours at about 95 to 100° C. using a temperature controlled oil bath. Approximately 12 mL of condensate water is collected in the Barrett receiver as a result of glucose oligomerization reaction and the aldol condensation reaction to give alkylation at the C1 position. The white suspension of sugar particles disappears as the reaction from glucose to APG proceeds until a clear solution is obtained. This demonstrates that the APG is soluble in the alcohol. The resulting APG solution is colorless, indicating that byproduct formation of colored bodies, such as furfurals, is minimized.

Provenance & Evidence