Oxidation of KMnO4: Necessity of Soluble Starting Material

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KMnO4 oxidation of benzylic methyl to acid can be inconsistent, with solubility of the starting material being a debated factor. While solubility is not strictly necessary for the reaction to occur, it can enhance the reaction rate. The reaction may still proceed at the interface of solid and liquid, albeit more slowly. Key considerations include the mole ratio of KMnO4 to the compound and the specific method of conducting the reaction, which can influence yield and overall efficiency.
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KMnO4 oxidation of benzylic methyl to acid sometimes does not proced. Is it necessary that solid starting material should soluble in this reaction mixture to proced the reaction.
 
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Is this an experimental result, or a hypothetical question? That is, is your question one of yield, as in why isn't the yield higher?

I don't think solubility is required, though helpful. Reaction can occur at interface, but more slowly. What is the mole ratio of KMnO4 to cmpd? How are you doing the reaction?
 

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