Abstract: Phenol and its derivatives are important intermediates in organic synthesis. This experiment combines the iodine anion catalyzed dehydroaromatization and the synthesis of m-cresol, aiming to develop it as a potential undergraduate organic chemistry experiment. This experiment used inexpensive and readily available 3-methyl-2-cyclohexen-1-one as the starting material, tetra-n-butylammonium iodide (n-Bu₄NI) as catalyst, and 1,2-dichloroethane as solvent to achieve the green synthesis of m-cresol. Subsequently, the product was purified via back extraction, followed by structure characterization and purity analysis. In short, the experiment is reasonable, reliable and straightforward, which includes the basic techniques such as inert gas protection, reflux, extraction, back extraction, filtration and distillation, as well as the organic compound characterization, making it highly suitable for undergraduate comprehensive experiments.

Key words: Iodide anion, Aromatization, Phenol, Green synthesis