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Acetonedicarboxylic acid

Acetonedicarboxylic acid is the organic compound with the formula . It is classified as both a dicarboxylic acid and an oxocarboxylic acid.

Preparation

Acetonedicarboxylic acid is prepared commercially by oxidation of citric acid. It can also be prepared by treating citric acid with fuming sulfuric acid.

Reactions and uses

Upon heating it undergoes decarboxylation first to give acetoacetic acid then acetone:

Acetonedicarboxylic acid and its esters such as dimethylacetonedicarboxylate are primarily used as building blocks in the synthesis of heterocycles One example is it use in Robinson's classic synthesis of tropinone. It participates in the Weiss–Cook reaction.

Related compounds

See also

References