Cinnamaldehyde from cinnamic acid

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Discussion Overview

The discussion centers around the conversion of cinnamic acid to cinnamaldehyde, exploring various synthetic routes and reagents. Participants consider the implications of reducing agents on the unsaturated carbon framework of the compound.

Discussion Character

  • Technical explanation
  • Debate/contested
  • Mathematical reasoning

Main Points Raised

  • One participant proposes converting cinnamic acid to cinnamaldehyde by first making it into an alcohol and then using PCC, but expresses concern about reducing the acid affecting the α β unsaturated carbons.
  • Another participant suggests that using a mild reducing agent may not disturb the unsaturated atoms.
  • There is a question about the suitability of NaBH4, Lindlar's catalyst, or Pd with BaSO4 for the reduction process.
  • A suggestion is made to use Lindlar's catalyst via Rosenmund reduction, with a hint left for further exploration.
  • Another participant recommends lithium tri(tertbutoxy)aluminum hydride, cautioning that using Pd reagents with hydrogen could lead to cross-reactivity with olefins.

Areas of Agreement / Disagreement

Participants express differing views on the choice of reducing agents and their potential effects on the unsaturated structure, indicating that multiple competing views remain without a consensus on the best approach.

Contextual Notes

There are unresolved considerations regarding the specific conditions under which each proposed reagent would operate effectively, as well as the potential for cross-reactivity with other functional groups.

deep838
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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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I don't think if you'll use a mild reducing agent, it will disturb unsaturated atoms.
 
AGNuke said:
I don't think if you'll use a mild reducing agent, it will disturb unsaturated atoms.

So will NaBH4 work? Or Lindlar's? Or Pd with BaSO4?
 
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.
 
AGNuke said:
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.

Thanks.
 
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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