This project describes the optimization of conditions for the palladium-catalyzed ortho-methoxylation reaction of diaryl ketoxime ethers.  For this optimization study, the methoxylation of O-methyl oxime ether of benzophenone [Ph2C=N-OCH3] was used. Several reactions have been run under different conditions (temperature, concentration, time, type of oxidant, amount of oxidant, amount of catalyst, and solvent) to optimize yield(s).  The reaction gives the (Z)-mono-, (E)-mono-, and di-methoxylated products, and the amounts of these three products can be modified depending on reaction conditions.  A palladacycle of the oxime ether of benzophenone has also been synthesized to help investigate the mechanism of this reaction.  Yields for this reaction with different substituents on the ring and with different alcohols will be discussed.

Ortho-alkoxylation of diaryl ketoxime ethers

247th National Meeting (2014)

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