The reactivity of o-hydroxybenzyl alcohol and derivatives in solution at elevated temperatures

The benzylic cation is the reactive intermediate in the thermal, liquid-phase degradation of o-hydroxybenzyl alcohol (o-HBA) in the presence of a catalytic amount of acid. This was gleaned from an investigation of the reactivity of o-HBA in various solvents. In alcoholic solvents, the benzylic cation reacts with the solvent to yield the corresponding ehers, while in apolar hydroaromatic solvents, o-cresol is formed via hydride transfer from the solvent to the benzylic cation.