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Cinnamaldehyde from cinnamic acid

by deep838
Tags: acid, cinnamaldehyde, cinnamic
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deep838
#1
Feb15-13, 04:03 AM
P: 105
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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AGNuke
#2
Feb15-13, 05:25 AM
PF Gold
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P: 456
I don't think if you'll use a mild reducing agent, it will disturb unsaturated atoms.
deep838
#3
Feb15-13, 06:21 AM
P: 105
Quote Quote by AGNuke View Post
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
#4
Feb15-13, 07:43 AM
PF Gold
AGNuke's Avatar
P: 456
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.
deep838
#5
Feb15-13, 07:48 AM
P: 105
Quote Quote by AGNuke View Post
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
#6
Feb15-13, 09:22 AM
Sci Advisor
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PF Gold
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P: 3,724
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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