Cinnamaldehyde from cinnamic acid

deep838

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?

AGNuke

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

deep838

Quote by AGNuke

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?

AGNuke

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.

deep838

Quote by AGNuke

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.

chemisttree

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.

Similar Threads for: Cinnamaldehyde from cinnamic acid
Thread	Forum	Replies
Phosphoric acid vs. Hydrochloric acid when removing rust and rerusting	Biology, Chemistry & Other Homework	5
Find the molecular mass of acid in acid base neutralization	Biology, Chemistry & Other Homework	6
Weak acid/strong base titration (Acetic acid/NaOH)	Biology, Chemistry & Other Homework	4
trans-cinnamic acid	Chemistry	1
Stereochemistry of Bromine Addition to trans-Cinnamic Acid	Chemistry	10

deep838	Cinnamaldehyde from cinnamic acid Tweet 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?

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

AGNuke	Cinnamaldehyde from cinnamic acid 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.

chemisttree Recognitions: Gold Member Homework Help Science Advisor	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.