Bis-salicylates are formed by the oxidation of o-phenoxybenzoic acids with persulphate. o-Phenoxybenzoic acid itself yields the unsymmetrical dimer, diphenyl 2,4′-dihydroxybiphenyl-3,3′-dicarboxylate, which is also obtained by a similar oxidation of phenyl salicylate. The reaction proceeds by rearrangement of the initial carboxyl radicals to o-(phenoxycarbonyl)phenoxyl radicals which then dimerise.
R. H. Thomson and A. G. Wylie, J. Chem. Soc. C, 1966, 321 DOI: 10.1039/J39660000321
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