Faust
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2-methyl, 3-indole acetic acid oxidation
Hi everyone,
I was wondering if there is appropiate way to oxidize the methyl in position 2 following by decarboxylation, without affecting acetic acid in
position 3 of indole ring.
I was thinking about protecting acid with methyl ester but then, KMnO4 won't be suitable because acidic and alkaline medium will break the ester.
shall K2Cr2O7 be suitable ? or other route ?
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bfesser
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Thread Moved
22-11-2013 at 07:48 |
Faust
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Any suggestions ? 
I busied myself to think of a story which would speak to the mysterious fears of our nature, and awaken thrilling horror. One to make the reader dread
to look around. To curdle the blood, and quicken the beatings of the heart.
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bfesser
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Just one: don't post in all boldface.
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Galinstan
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Im no expert so correct me if im wrong but i don't think you can oxidise your methyl group to a carboxylic acid with kmno4 in this case. it would
probably just destroy the ring, unless you have any evidence to support your suggested synthesis i don't think it can be done
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Faust
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Fair enough
I busied myself to think of a story which would speak to the mysterious fears of our nature, and awaken thrilling horror. One to make the reader dread
to look around. To curdle the blood, and quicken the beatings of the heart.
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Faust
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Quote: Originally posted by Galinstan  | | Im no expert so correct me if im wrong but i don't think you can oxidise your methyl group to a carboxylic acid with kmno4 in this case. it would
probably just destroy the ring, unless you have any evidence to support your suggested synthesis i don't think it can be done |
I don't think so, because it's possible to oxidize indole -2-methanol into indole -2- carboxaldehyde by Pot. permanganate in acetone, but no ring
cleavage .
http://www.orgsyn.org/demo.aspx?prep=cv5p0567
thank you for sharing
I busied myself to think of a story which would speak to the mysterious fears of our nature, and awaken thrilling horror. One to make the reader dread
to look around. To curdle the blood, and quicken the beatings of the heart.
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zed
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Indole Acidic Acid can be readily produced by a number of methods.
Producing it from 2-Methyl-Indole Acetic Acid, is unlikely.
It would be nice, since the route>Phenylhydrazine+Levulinic Acid>Phenylhydrazone. And, Phenylhydrazone +ZnCl+heat> 2-Methyl-Indole Acetic
Acid. Easy and Inexpensive.
Alas, it is unlikely that you can oxidize the two position to a carboxyl.
If you have a pressure reactor, and Indole, synthesis is straightforward. Likewise, I have seen patents utilizing Ethyl-Acrylate, Acetic Anhydride,
and heat. The 3 position of the Indole ring is remarkably easy to Alkylate. Though obtaining the Indole starting material may be a problem for some.
Not a problem if you have Phenylhydrazine however. You can make your own Indole.
Check the search engine. Check Organic Synthesis Online.
Oxidizing an alcohol to an aldehyde requires very mild conditions. Oxidizing a Methyl to a Carboxyl, is an entirely different animal. In general,
once you get to oxidizing things, it's damned hard to stop the process.
You can try it, but there is a good chance you will end up with O-Nitro-Benzoic Acid, or some such thing.
[Edited on 27-11-2013 by zed]
[Edited on 27-11-2013 by zed]
[Edited on 27-11-2013 by zed]
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