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Author: Subject: Aldol Condensation of Piperonal with Acetone
Ephoton
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[*] posted on 10-1-2010 at 05:38
wolff kishner


the aldol does work on piperonal and in reasonable
yeild in the documents I have read.

the one thing that piperonal does not do is form an alpha
methyl butenone if formed by the acid condensation with
MEK.

both acid and base condensation give the same product.

having said this if you were to use acetone as stated above
the preform a wolff kishner you would have an alkene that
would oxidize too mdp2b not too bad realy.




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Klute
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[*] posted on 10-1-2010 at 06:33


The same product from acid or base catalysis? Do you have a ref for that? I'm quite surprised.

What is possible is that the double condensation product is obtained with acid catalysis like veratraldehyde and vanillin, as claimed by this document.

Although it's a waste of piperonal, teh double condensation product will give a ester that hydrolyzes to MDP2P, and MDcinnamic acid.




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[*] posted on 10-1-2010 at 16:20


"both acid and base condensation give the same product."

This is simply not true.





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[*] posted on 10-1-2010 at 19:21


sorry you are right :(
it was a long time ago I read that and played with aldol.




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Klute
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[*] posted on 18-1-2010 at 12:30


here is a patent were they do the aldol between piperonal and acetone, then hydrogenate the product to Cassione, aka 4-(3,4-methylenedioxyphenyl)butan-2-one, the aroma of Cassis.

See the description here:http://www.thegoodscentscompany.com/data/rw1012851.html

Synthesis of Medroxalol intermediates - US Patent 4697024

This ketone could actually be used to make HMDMA, a derivative of MDMA, see: Indentification of N-Methyl-4-(3,4-Methylenedioxyphenyl)Butan-2-Amine, Distributed as MBDB

I would pretty much just keep it as is though, smells nice :)

[Edited on 18-1-2010 by Klute]




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[*] posted on 27-1-2010 at 21:04


Quote: Originally posted by Klute  

This ketone could actually be used to make HMDMA, a derivative of MDMA, see: Indentification of N-Methyl-4-(3,4-Methylenedioxyphenyl)Butan-2-Amine, Distributed as MBDB
[Edited on 18-1-2010 by Klute]


I saw a paper that said HMDMA substitutes for MDMA in 5/7 rats at about six times the dose of MDMA. I was surprised [that it substituted for MDMA at any dose].

[Edited on 28-1-2010 by Bolt]
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[*] posted on 28-1-2010 at 02:29


:P
By extrapolation that gives an active dose of 600-800mg. Then it's really better to leave it in the olfactorily pleasing ketone state than to transform it into the fishy/bitter amine state. I would have been surprised if it was more active. I always was under the impression that the phenethylamine substructure does not allow for much variation for amphetamine like effects. My guess would have been that it is not active at all - and who knows what it really does.
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