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Issue 4, 1999
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The radical-induced decomposition of 2-methoxyphenol

Abstract

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 kuni (s–1) = 1015.2 ± 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.

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Article information


J. Chem. Soc., Perkin Trans. 2, 1999, 777-780
Article type
Paper

The radical-induced decomposition of 2-methoxyphenol

E. Dorrestijn and P. Mulder, J. Chem. Soc., Perkin Trans. 2, 1999, 777
DOI: 10.1039/A809619H

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