2-Iodoxybenzoic Acid Synthesis Essay


InChI = 1S/C7H5IO4/c9-7-5-3-1-2-4-6(5)8(10,11)12-7/h1-4,10H


(oxidizing agent, single-electron-transfer reagent)1

Alternate Name:o-iodoxybenzoic acid; 1-hydroxy-1,2-benziodoxol-3(1H)-one-1-oxide, IBX.

Physical Data: mp 232–233 °C.

Solubility: soluble in DMSO, DMSO/THF mixtures; insoluble in H2O and most organic solvents.

Analysis of Reagent Purity:1H-NMR (DMSO-d6) δ 8.15 (d, 1H), 8.01 (d, 1H), 7.98 (t, 1H), 7.84 (t, 1H). 13C-NMR (DMSO-d6) δ167.49, 146.59, 133.39, 132.97, 131.36, 130.10, 124.99.2

Preparative Methods: not commercially available. IBX was first synthesized in 1893,2 and is the penultimate precursor of the Dess-Martin periodinane reagent.3, 4 IBX is prepared by the slow addition (0.5 h) of potassium bromate (76.0 g, 0.45 mol) to a rapidly stirred sulfuric acid mixture (0.73 M, 730 mL) containing 2-iodobenzoic acid (85.2 g, 0.34 mol). The reaction temperature is maintained below 55 °C until addition is complete. The reaction mixture is heated to 65 °C for 3.6 h. The flask is cooled to 0 °C, and the solid is filtered and washed with water (1000 mL) and ethanol (2 × 50 mL) to afford IBX in 93–98% yield.3, 4 An additional ether wash (3 × 50 mL) is beneficial.5 Other oxidants such as potassium permanganate,2chlorine,6 or oxone7 can also be employed.

Handling, Storage, and Precautions: moisture stable, explosive under excessive heating (> 200 °C) or impact.8

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