Benz But Doesn’t Break. Part IV

The second part of the modified benzilic acid synthesis project was as straightforward as the first part was complicated. The quantities of ammonium nitrate for the copper(II) acetate catalyzed oxidation were adjusted for the different molecular weight of the starting material. Other than that conditions were the same as for the benzoin to benzil transformation. The great part about this step is that both the 4,4’methybenzoin and deoxy 4,4’methybenzoin were oxidized to 4,4’methybenzil. The products were obtained in good yields and the crystals were generally “fluffy” and easily handled. IR, UV, GC-FID and NMR analysis were performed. Benzil analogues have be studied as carboxyesterase inhibitors. Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterasesInhibition of carboxylesterases by benzil (diphenylethane-1,2-dione) and heterocyclic analogues is dependent upon the aromaticity of the ring and the flexibility of the dione moiety. DMBenzoin_oxidationDMBenzil_NMR

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