The Kolbe-Schmitt Reaction in Aqueous Solutions

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  • MORINAGA Naoki
    Advanced Organic Material Chemistry, Department of Material Science, Faculty of Science & Engineering, Shimane University
  • UCHIGASHIMA Mikiko
    Advanced Organic Material Chemistry, Department of Material Science, Faculty of Science & Engineering, Shimane University
  • RAHIM Mohammad Abdur
    Advanced Organic Material Chemistry, Department of Material Science, Faculty of Science & Engineering, Shimane University
  • ONISHI Kazutoshi
    Advanced Organic Material Chemistry, Department of Material Science, Faculty of Science & Engineering, Shimane University
  • TAKAHASHI Kazufumi
    Advanced Organic Material Chemistry, Department of Material Science, Faculty of Science & Engineering, Shimane University
  • KOSUGI Yoshio
    Advanced Organic Material Chemistry, Department of Material Science, Faculty of Science & Engineering, Shimane University

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  • 水溶液中におけるコルベ · シュミット反応

Description

The carboxylation of m-aminophenol with potassium hydrogencarbonate in aqueous solutions has been studied kinetically. The formation of 4-hydroxyanthranilic acid (4HAA) has been found for the first time in the carboxylation of m-aminophenol which gives only p-aminosalicylic acid (pAS) in the usual Kolbe-Schmitt reaction. Since 4HAA was easily decarboxylated, the product was removed from the reaction mixture after the carboxylation for 1 h at 60 °C. This method was repeated three times and 4HAA was obtained as a major product in 30.2% yield.

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