Effect of Quaternary Ammonium Salt on the Carboxylation of Active Methylene Compounds with Carbon Dioxide in the Presence of Base

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  • DOUNO Reizo
    Departmento f Applied Chemistry, Himeji Institute of Technology;
  • YAMAUCHI YO
    Departmento f Applied Chemistry, Himeji Institute of Technology;
  • HAKUSHI Tadao
    Departmento f Applied Chemistry, Himeji Institute of Technology;

Bibliographic Information

Other Title
  • 塩基触媒による活性メチレン化合物のカルボキシル化における第四級アンモニウム塩の添加効果

Description

The effect of the ammonium salt on the carboxylation of indene, fluorene and acetophenone with carbon dioxide was examined in the presence of carbonates, phosphates or acetates as a base.<BR>The carboxylation of these active methylene compounds was remarkably promoted by the addition of benzyltributyl- and benzyltriethylammonium chlorides in the presence of IC, CO, at room temperature under the CO, pressure of 5kg/cm2.1, 3-Indenedicarboxylic acid, 9-fluorenecarboxylic acid and benzoylacetic acid were obtained in good yields. The yield of the carboxylated products varied with the counter anion of the ammonium ion in the order: Cl->Br->I- > ClO4-.<BR>Although indene was effectively carboxylated by using CH3CO2K, fluorene and acetophenone were scarcely carboxylated under the similar conditions. Potassium phosphate caused the carboxylation of these active methylene compounds in considerable yields. Sodium carbonate and acetate proved to be poorer base than the corresponding potassium salts.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1982 (5), 811-817, 1982-05-10

    The Chemical Society of Japan

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