Traditionally, 1-ethynycyclohexanol was hydrated to produce 1-acetyl-1-cyclohexene under acidic conditions, using glacial acetic acid and sulfuric acid (C2H4O2/H2SO4). When pyridinium ionic liquids were substituted for the acetic acid solvent, the reactions were less exothermic. The yields for this hydration were found to be similar to that of the original system. This investigation also involved the synthesis of three ionic liquids containing the n-octylpyridine ([opy]+), n-nonylpyridine ([npy]+) and n-decylpyridine ([dpy]+) cations coupled with boron tetrafluoride anion ([BF4]-). These ionic liquids were substituted for the solvent in this reaction to provide a greener process. Previous studies suggest ionic liquids can be recycled or reclaimed. Ionic liquids can also stabilize intermediates better than traditional solvents as well as increase typical product yields.

Synthesis of 1-acetyl-1-cyclohexene using ionic liquids

255th National Meeting (2018)

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