The radical-induced decomposition of 2-methoxyphenol

The thermolysis of 2-methoxyphenol has been studied between 680 and 790 K, applying cumene as a radical scavenger. Two pathways were observed: a homolytic route involving the cleavage of the methoxyl O-C bond; leading to methane and 1,2-dihydroxybenzene, obeying k(uni) (s(-1)) = 10(15.2) (+/- 0.2) exp(- 239 +/- 8 (kJ mol(-1))/RT), and an induced route starting with abstraction of the phenolic hydrogen by cumyl radicals. After intramolecular hydrogen transfer a cascade of reactions yields phenol, 2-hydroxybenzaldehyde, and 2-hydroxybenzyl alcohol. The latter compound decomposes instantaneously into o-quinone methide (o-QM) which is reduced to o-cresol.