- Synthesis of Diacetyl-D-tartaric anhydride
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Diacetyl-D-tartaric anhydride could be produced through the following synthetic routes.
In a 500-ml. three-necked round-bottomed flask fitted with a liquid-sealed stirrer and two reflux condensers is placed 40 g. (0.27 mole) of anhydrous, powdered d-tartaric acid. A solution of 1.2 ml. of concentrated sulfuric acid in 136 g. (126 ml., 1.33 moles) of acetic anhydride is added, and the stirrer is started. The mixture warms up, and the tartaric acid goes into solution. The solution is heated gently under reflux with stirring for 10 minutes. The solution is poured into a beaker and cooled for 1 hour in an ice bath. The crude crystalline product is collected on a 15-cm. Büchner funnel, washed twice with 20-ml. portions of dry benzene, stirred mechanically with 175 ml. of cold absolute ether, filtered, and placed in a vacuum desiccator over phosphorus pentoxide and paraffin shavings for 24 hours. The yield of diacetyl-d-tartaric anhydride is 41–44.5 g. (71–77%), m.p. 133–134°, [α]D20 97.2° in dry chloroform (c = 0.47).
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