Anisole hydrolysis in high temperature water

We investigated the hydrolysis of anisole to phenol in high-temperature water with and without water-tolerant Lewis acid catalysis. With no catalyst present, anisole hydrolyzes to phenol in 97% yield after 24 hours at 365 °C, our experimentally determined optimal temperature and time. Experiments with varied water density and analysis of comparable literature data suggest that anisole hydrolysis is almost third order in water, when the S N 2 mechanism dominates. Of the water-tolerant Lewis acid catalysts studied, In(OTf) 3 offered the best phenol yield. Anisole hydrolysis was first order in catalyst and first order in substrate. Introducing In(OTf) 3 catalysis lowered the activation energy for anisole hydrolysis to 31 ± 1 kcal mol −1 . Anisole hydrolysis in high-temperature water with In(OTf) 3 catalysis is competitive with other techniques in the literature based on rate and yield. In the presence of 5 mol% In(OTf) 3 catalyst, anisole hydrolyzes to phenol in 97% yield after 90 minutes at 300 °C. We investigated the hydrolysis of anisole to phenol in high-temperature water with and without water-tolerant Lewis acid catalysis.