Selective removal of phenolic groups in certain dihydroxytoluenes by tetrazole ether formation and hydrogenolysis

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Abstract
Selectivity and yield were studied in the reaction of 5-chloro-1-phenyltetrazole with dihydroxytoluene systems. The mono-ethers of 2-methylhydroquinone (1a), 3-methylcatechol (2a), and 4-methylcatechol (3a) were formed in moderate yields with the predominant isomer resulting from attack by the more nucleophilic anion. With 1a and 2a, steric effects diminished the amount of predominant isomer formed as compared to 3a. The di-(1-phenyltetrazole) ethers were formed in good yields. Hydrogenolysis of mono- and di-ethers gave good yields of cresols and toluene as determined by gas chromatography and ultraviolet analysis, respectively.

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