2-Furanmethanediol Diacetate

Abstract

The reaction was carried out in a 300-ml Claisen flask having a 10-cm Vigreux column; 102 g (1 mole) of acetic anhydride was mixed with 0.1 ml (Note 1) of concentrated sulfuric acid with agitation by hand. Shaking was continued while the flask was cooled in an ice bath to 10°and 96 g (1 mole) of freshly distilled 2-furaldehyde, b.p. 157–163°, was added (over a period of ten minutes). The temperature was maintained at 10-20°. When the addition was complete and the contents of the flask had been well mixed, the cooling bath was removed and the mixture was allowed to get warm, which it did spontaneously with the heat of reaction; after about five minutes the temperature generally reached about 35°. When the temperature had fallen to that of the room (20–30 minutes), 0.4 g (Note 1) of anhydrous sodium acetate was added and the mixture was vacuum-distilled from an oil bath. The first fraction was collected at 50–140°/20 mm (50–70 g); it consisted mainly of acetic anhydride, 2-furaldehyde, and 2-furanmethanediol diacetate (Note 2). The main product came over at 140–142°/20 mm; it amounted to 129–139 g (65–70%). The distillate solidified completely; m.p. 52–53° (Note 3).