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Cinnamaldehyde from cinnamic acid

  1. Feb 15, 2013 #1
    Can somebody please tell me how to convert cinnamic acid to cinnamaldehyde? I was planning to first make it into the alcohol and then use PCC, but then wondered that reducing the acid might also reduce the α β unsaturated carbons too. Is there any reagent that would do the trick without causing any further troubles?
     
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  3. Feb 15, 2013 #2

    AGNuke

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    I don't think if you'll use a mild reducing agent, it will disturb unsaturated atoms.
     
  4. Feb 15, 2013 #3
    So will NaBH4 work? Or Lindlar's? Or Pd with BaSO4?
     
  5. Feb 15, 2013 #4

    AGNuke

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    If you want to use Lindlar, do it so via Rosenmund reduction. I leave the work up to you, now you have got the hint.
     
  6. Feb 15, 2013 #5
    Thanks.
     
  7. Feb 15, 2013 #6

    chemisttree

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    I would go with lithium tri(tertbutoxy)aluminum hydride under these conditions.

    Any time you use Pd reagents with hydrogen you risk some cross reactivity with olefins.
     
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