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Synthesis 1990; 1990(7): 612-614
DOI: 10.1055/s-1990-26958
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New and Efficient Conversion of Benzoic Acids into Salicylic Acids via Copper Mediated Hydroxylation Process

Olivia Reinaud* , Patrice Capdevielle, Michel Maumy
  • *Laboratoire de Recherches Organiques de l'ESPCI, associé au CNRS, 10 rue Vauquelin, F-75231 Paris Cedex 05, France
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Publication History

Publication Date:
17 September 2002 (online)

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N-benzoyl-2-methylalanines 3, obtained through condensation of aroyl chlorides 1 with sodium 2-methylalaninate are ortho-hydroxylated by the new Cu(0)/O2/trimethylamine N-oxide system. Acid hydrolysis of the so-obtained salicylamides 4 provides salicylic acids 5 in excellent yield. When the substrate contains three electron-releasing groups the yields are moderate.

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