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Topic: Acid into an Aldehyde?  (Read 3886 times)

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Offline chrisbb

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Acid into an Aldehyde?
« on: April 10, 2008, 08:43:33 PM »
Hello people.
Is it possible to convert a carboxylic acid (like benzoic acid), in to the aldehyde (benzaldehyde)? I've looked around online as well as in my organic text book (McMurry 7th ed). any ideas?

Thanks :)
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Offline english

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Re: Acid into an Aldehyde?
« Reply #1 on: April 10, 2008, 08:51:42 PM »
Perhaps by converting the acid into an acyl compound and then displacing the leaving group with hydride (acyl addition-elimination).
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Offline ARGOS++

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Re: Acid into an Aldehyde?
« Reply #2 on: April 10, 2008, 09:06:50 PM »

Dear Chrisbb;

Rosenmund,  -  is one part of one answer!
(Thionyl-Chloride/DMF a add. Hint.)

You may take a view on:  "Rosenmund-Reduction”


Good Luck!
                    ARGOS++
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Offline chrisbb

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Re: Acid into an Aldehyde?
« Reply #3 on: April 11, 2008, 05:24:52 PM »
What i was trying to get, was one reagent that i could write down on paper that would reduce the acid to the aldehyde.. The only way i thought of (longer way):

Acid w/ LiAlH4 --> 1o OH --> treat w/ PCC.

Would that look ok?
I acn draw it out if it helps too :)
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Offline macman104

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Re: Acid into an Aldehyde?
« Reply #4 on: April 11, 2008, 05:27:52 PM »
Yes, that would work.
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