C. Boldron, P. Gamez, Duncan M. Tooke
Jun 6, 2005
Citations
0
Influential Citations
32
Citations
Journal
Angewandte Chemie
Abstract
Substituted hydroxybenzaldehydes are important feedstock materials for the pharmaceutical and perfume industries. These compounds are commonly made by the selective oxidation of aromatic methyl groups. However, this chemical reaction is difficult and often proceeds to the carboxylic acid derivative. Thus, 4-hydroxy-3,5-dimethylbenzaldehyde (HDB) is a valuable intermediate, especially for the preparation of drugs. A number of synthetic routes to HDB starting from 2,4,6-trimethylphenol (TMP) involving stoichiometric amounts or an excess of oxidant are known. So far, the only catalytic oxidation of TMP to HDB was achieved by Takehira and co-workers. Copper-containing enzymes, such as vanillyl alcohol oxidase or laccase can selectively produce the aromatic aldehyde functional group from a methyl group. We report here a bioinspired Cu/neocuproine system to perform the selective para-formylation of mesitol [Eq. (1)]. The reaction