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Theoretically possible to reduce m-nitrophenone to 3-ethylnitrobenzene -H2,Pd/C,45psi

  1. Jul 25, 2010 #1
    Is there anyway that a Ketone on a benzene ring could be reduced to a hydrocarbon with the use of H2, Pd/C, 45 psi ? I know that carbonyls on aromatic rings are able to be reduced to alcohols via this method but would be interested in if it is possible (more so then practical) to fully reduce to a hydrocarbon w/ the listed reagents. I did some searching and may have found some articles which stated that it may be possible with quite a long reaction period. If this method wont would any variations of it suffice? Suppose H2 Nickel or Raney? Maybe increase in psi or temp?

    Thanks for the help guys!
     

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  3. Jan 29, 2017 #2

    TeethWhitener

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    A ketone on a benzene ring will be reduced with catalytic hydrogenation under pressure. However, in reference to the title of this thread, I'd also point out that a nitro group will be reduced to an amine under the same reaction conditions. So instead of going from m-nitrophenone to 3-ethylnitrobenzene, you'd most likely get 3-ethylaniline as your product instead. (EDIT: it's also possible to reduce the benzene ring to a cyclohexane under exposure to these types of conditions. It's better to look into something like a Wolff-Kischner reduction or a Clemmensen reduction to get an aromatic ketone to an alkane.)
     
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