Alkoxyhydrosilane-facilitated cross-etherification reaction of secondary benzyl alcohol with aliphatic alcohol: synthesis of unsymmetrical dialkyl ethers.

Alkoxyhydorosilane is found to be an effective mediator for the cross-etherification reaction between two distinct alcohols, namely, a secondary benzyl alcohol and an aliphatic alcohol, providing the unsymmetrical dialkyl ethers in good-to-high yields. The reaction is also successfully applied to the lignin model compound, which is an important renewable non-fossil organic carbon source. Initial mechanistic studies indicated that the carbocation derived from benzyl alcohol was formed under the present reaction conditions.