Reaction of Aliphatic Dicarboxylic Acids with Acyl Chlorides in the Presence of Aluminum Chloride

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The treatment of succinic acid with lauroyl or stearoyl chloride gave the five-membered β-diketone (II) substituted with a long chain at the α-position, together with a trimer (III) of the acyl chloride. Bicyclo[3.3.1]nonane-2, 4-dione (VI) substituted with a methyl or ethyl group at the C₃-position was prepared from cyclohexane-1, 3-dicarboxylic acid (V) and propionyl or butyryl chloride, respectively. D-Camphoric acid afforded an unexpected product, 4-acyl-2, 2, 3-trimethyl-3-cyclopentenecarboxylic acid (IX), on reaction with acyl chloride. Although acetyl chloride gave no product on treatment with succinic acid, it afforded 3-acetylbicyclo[3.2.1]octane-2, 4-dione (XI), 3-acetylbicyclo[3.3.1]nonane-2, 4-dione (VId), and 2-acetylcyclohexane-1, 3-dione (XII) on reaction with the corresponding dicarboxylic acids.