Cinnamaldehyde from cinnamic acid

  • Thread starter deep838
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In summary, to convert cinnamic acid to cinnamaldehyde, one can use a mild reducing agent such as NaBH4 or Lindlar's or Pd with BaSO4. However, if using Lindlar's, it is recommended to use Rosenmund reduction. Another option is to use lithium tri(tertbutoxy)aluminum hydride, but there is a risk of cross reactivity with olefins if using Pd reagents with hydrogen. It is suggested to carefully consider the choice of reducing agent to avoid any potential issues.
  • #1
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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  • #2
I don't think if you'll use a mild reducing agent, it will disturb unsaturated atoms.
 
  • #3
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?
 
  • #4
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.
 
  • #5
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.
 
  • #6
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.
 

What is cinnamaldehyde?

Cinnamaldehyde is a naturally-occurring organic compound found in the bark of cinnamon trees. It is responsible for the characteristic flavor and aroma of cinnamon.

How is cinnamaldehyde produced from cinnamic acid?

Cinnamaldehyde can be produced through a chemical reaction called the Perkin reaction, in which cinnamic acid is heated with an aldehyde compound. Alternatively, it can be extracted from cinnamon bark using steam distillation.

What are the uses of cinnamaldehyde?

Cinnamaldehyde has a variety of uses, including as a flavoring agent in food and beverages, a fragrance in perfumes and cosmetics, and a preservative in some pharmaceutical products. It also has potential medicinal properties, such as anti-inflammatory and antimicrobial effects.

Is cinnamaldehyde safe for consumption?

In small amounts, cinnamaldehyde is generally considered safe for consumption. However, it may cause irritation or allergic reactions in some individuals. It is important to consult with a healthcare professional before consuming cinnamaldehyde in large amounts or if you have any known allergies or sensitivities.

Is cinnamaldehyde environmentally friendly?

Cinnamaldehyde is considered to be a more environmentally friendly alternative to synthetic fragrances and preservatives. However, its production can still have negative impacts on the environment, and it is important to use and dispose of products containing cinnamaldehyde responsibly.

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