Abstract
A convenient two-step protocol preparation of ortho-alkylated (substituent with the carbomethoxy group at the end of five carbon atoms alkyl chain) aromatic carboxylic acids from benzoic acids anilides is described. Ortho-lithiation of benzanilides and subsequent reaction of the generated bis(N- and C-ortho-)-lithiated anilides with aromatic aldehydes provided 3-arylphthalides. In the next step, these phthalides were converted into 5-(2-carboxyphenyl)-5-phenylpent-2-enoic acids by treatment with 1-methoxy-1-trimethylsilyloxybuta-1,3-diene.
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