Crystals of 2-iodobenzoic acid that crystallized out from the reaction mixture.
2-iodobenzoic acid is a quite easy to prepare chemical, made from anthranilic acid by the Sandmeyer reaction. It starts with the diazotization of anthranilic acid followed by a diazo replacement. First anthranilic acid is treated with nitrous acid in order to convert the amino group into the diazo group. The diazo group is ejected, yielding a carbocation which is then attacked by highly nucleophilic I− anion.
From o-iodobenzoic acid several chemicals could be made, on of these and probably one of the most famous is the IBX and the Dess-Martin Periodane.
Dess–Martin periodinane (DMP) is a chemical reagent used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones. Compared to other reagents, it has several advantages that include milder conditions (room temperature, neutral pH), shorter reaction times, higher yields, simplified workups, high chemoselectivity, tolerance of sensitive functional groups, and a long shelf life. It is named after the American chemists Daniel Benjamin Dess and James Cullen Martin who developed the reagent in 1983.
It’s produced with a two step reaction, involving the oxidation of the iodine atom of the corresponding benzoic acid with Oxone or potassium-bromate and sulfuric acid, than treating the resulting IBX (2-iodoxybenzoic acid) with acetic anhydride. The only bad point in the synthesis, that the IBX and the DMP could explode if not treated properly.