Differing selectivities in mechanochemical versus conventional solution oxidation using Oxone

A mechanochemical oxidation of methoxylated aromatic chemicals is described, providing an example of a very different selectivity as compared to solution-based chemistry. Oxone was shown to react with 1,2,3-trimethoxybenzene to yield predominantly 2,6-dimethoxybenzoquinone in the solid state or 2,3,4-trimethoxyphenol in solution. The difference in effective acidity of the reaction conditions was not apparently responsible for the observed selectivity. The mechanochemical method described is simple, reproducible, and gave higher yield at higher conversion of substrate compared to solution conditions.