Acetonedicarboxylic Acid [542-05-2-A] C5H6O5
In a 500-ml flask, mix 60 ml of glacial acetic acid and 43 ml of acetic anhydride. Place the flask in an ice/salt cooling bath and add 40 g (0.27 mol) of acetonedicarboxylic acid while stirring, maintaining the temperature below 10 °C until the reaction is complete. The acetonedicarboxylic acid slowly dissolves, and a pale yellow precipitate forms. If the precipitate does not appear within 3 hours, add some benzene. Filter off the solid product and wash with 30 ml of glacial acetic acid and 100 ml of benzene. Dry the acetonedicarboxylic acid under high vacuum to yield 30 g of the product. Alternatively, it can be dried on a clay plate in the air. The dry product forms a white powder with a melting point of 137-138 °C. The yield corresponds to 86% of the theoretical yield.
Description: Acetonedicarboxylic acid forms a fine, white, water-insoluble powder. It is an important component for the total synthesis of the local anesthetic cocaine.
Source: Peter C. Meltzer et al, J. Med. Chem. 2001, 44, 2619-2635
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Last updated: 02/08/2006
Other names: Glutaric acid anhydride; β-Ketoglutaric acid anhydride; 3-Oxoglutaric acid anhydride; 3-Oxopentanedioic acid anhydride; 2H-Pyran-2,4,6(3H,5H)-trione; Pyran-2,4,6-trione