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Synthesis 2000; 2000(11): 1603-1607
DOI: 10.1055/s-2000-7610
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Application of Organolithium and Related Reagents in Synthesis, Part 24. Synthetic Strategies Based on Aromatic Metallation. A Concise Regiospecific Conversion of Benzoic Acids into 2-(1-Aryl-2-methoxycarbonylethyl)benzoic Acids

Jan Epsztajn* , Adam Bieniek, Justyna A. Kowalska, Krystyna K. Kulikiewicz
  • *Department of Organic Chemistry, University of Łódź, 90-136 Łódź, Narutowicza 68, Poland; Fax + 48 (42) 6 78 65 83; E-mail: epsztajn@krysia.uni.lodz.pl
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Publication Date:
31 December 2000 (online)

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The synthesis of the 3-arylphthalides 3 via metallation (BuLi) of the benzanilides 1 and subsequent reaction of the generated bis-lithiated anilides 2 with aromatic aldehydes is described. Conversion of 3 into the corresponding 2-(1-aryl-2-methoxycarbonylethyl)benzoic acids 4 by treatment with 1-methoxy-1-trimethylosiloxyethene in the presence of titanium tetrachloride, as a way of regiospecific transformation of benzoic acids, is also described.

lithiation - anilides - phthalides - silyl enol ethers - benzoic acids

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