Synthesis and regiospecific deoxygenation of β-resorcylic ester derivatives to 4-hydroxybenzoates

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Abstract
Ethyl [carboxy,6-14C2]-4-hydroxy-2-methyl-(6a), and -2,3,5-trimethyl-benzoate (6b), together with ethyl 4-hydroxy-2,3-dimethylbenzoate (6c), have been prepared in satisfactory yields by deoxygenation of the corresponding resorcylate esters, (5a–c), respectively, via hydrogenolysis of their 4-benzyloxy-2-(1-phenyl-1H-tetrazolyloxy)-derivatives, (8a–c). Ethyl 2,4-dihydroxy-5,6-dimethyl-3-trideuteriomethylbenzoate (5d) has been synthesised by trideuteriomethylation of ethyl 2,3-dimethyl-4,6-dioxocyclohexanecarboxylate (10c), followed by dehydrogenation. Preparations of the requisite resorcylate derivates are included.

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