Upjohn dihydroxylation

What is Upjohn Dihydroxylation?

The Upjohn dihydroxylation is a chemical reaction used to introduce two hydroxyl groups onto an aromatic ring. It was developed by Dr. William Upjohn in the 1930s and has since become a widely used method in organic synthesis..

The reaction involves the use of osmium tetroxide (OsO4) as a catalyst, along with a peroxide, such as hydrogen peroxide (H2O2) or tert-butyl hydroperoxide (TBHP), and a solvent, such as an alcohol or water. The aromatic compound is treated with these reagents, resulting in the formation of two hydroxyl groups on the aromatic ring..

One of the main advantages of the Upjohn dihydroxylation is that it allows for the selective introduction of hydroxyl groups onto an aromatic ring, without affecting any other functional groups present. It is also a useful method for synthesizing a variety of compounds, including flavonoids and other natural products..

However, there are also some limitations to the Upjohn dihydroxylation. It requires the use of toxic and expensive reagents, such as OsO4, and can be sensitive to the conditions of the reaction. In addition, the reaction may not always be efficient, and may produce low yields in some cases..

Despite these limitations, the Upjohn dihydroxylation remains a valuable tool in the synthesis of compounds containing hydroxyl groups, and has been used in the synthesis of a variety of chemicals, including pharmaceuticals, fragrances, and dyes..