The Vespiary

The Hive => Newbee Forum => Topic started by: nautilus on June 06, 2004, 08:11:00 PM

Title: MDMA from Coffee? Non-listable precursor! :-)
Post by: nautilus on June 06, 2004, 08:11:00 PM
Look what I found while buying the stuff for my eugenol experiments...
I used TFSE for kaffeesaure, Kaffeesäure and coffee combined with acid, and didn't find anything that looks like this, so I thought I should mention it.

This is 'kaffeesäure' or 'coffee acid':
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000511810-caffeesaure.gif)

I first read about it here:

http://www.fslemi.uni-bonn.de/gewuerze/html/stralsklasse/sel.html (http://www.fslemi.uni-bonn.de/gewuerze/html/stralsklasse/sel.html)



References are here

http://www.paracelsus.de/heilv/natur_177.html (http://www.paracelsus.de/heilv/natur_177.html)

and here

http://www.g-netz.de/Health_Center/heilpflanzen/zzwirkstoffe/phenolsaeuren.shtml#phenolsaeuren (http://www.g-netz.de/Health_Center/heilpflanzen/zzwirkstoffe/phenolsaeuren.shtml#phenolsaeuren)

.
The latter also has a list of sources (other than the obvious considering the name).

Other names appear to be 3,4-Dihydroxyzimtsäure (= 3,4-dihydroxycinnamaldehyde) and 3-O-Caffeoyl-D-chinasäure, but I haven't found it in the 84th edition of the CRC.
Searching on the web it appears to be freely availabe in pure form(5 g = 19 euros at the first site I found it). Take note: you have to type the a-umlaut (ä) correctly in order to find anything in Google.

Am I on to something here, or am I just really showing my newbee status in an almost obscene way?  :P

The real question is: is it economically and practically feasible to change the carboxyl group to a methyl group (either before or after methylenation of the hydroxyl groups on the road to safrole, as described

here (https://www.thevespiary.org/rhodium/Rhodium/chemistry/methylenation.html)

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/methylenation.html).

The moving of the double bond can of course be found

here (https://www.thevespiary.org/rhodium/Rhodium/chemistry/isomerizafrole.html)

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/isomerizafrole.html).

I don't have the knowledge to answer this question yet, hope you can help.

Title: caffeic acid
Post by: gsus on June 06, 2004, 09:01:00 PM
caffeic acid.

Title: Nomenclature clash
Post by: nautilus on June 06, 2004, 09:22:00 PM
Ahaaaaa!

Thanks

It's fun though, putting the pieces together for myself, a great learning experience!

Title: I wonder what a little ozonolysis would do....
Post by: ning on June 06, 2004, 09:58:00 PM
Perhaps we at the hive would have a use for some 3,4-dihydroxybenzaldehyde....?

Ozone, or perhaps KMnO4 under certain conditions?

Title: Mentioned before
Post by: Aurelius on June 06, 2004, 09:59:00 PM
do a search:

Post 122772 (https://www.thevespiary.org/talk/index.php?topic=12530.msg12277200#msg12277200)

(dormouse: "MDA from Coffee  -Wizard X", Serious Chemistry)

Post 323392 (https://www.thevespiary.org/talk/index.php?topic=11299.msg32339200#msg32339200)

(mellow: "MDP2P from waste vegetation?", Novel Discourse)

Title: You also have the trouble that you end up with
Post by: _mu_ on June 07, 2004, 12:04:00 AM
You also have the trouble that you end up with a carboxylic acid. To get that group converting to something useful, you need serious chemistry. When you have access to those things, why not order a less troublesome precursor? :-)
Title: hmmm ... coffee as a listed chemical
Post by: former_chemist on June 07, 2004, 10:17:00 AM
I knew it was only a matter of time!

This is definitely a synth whose time has come.
Changing a carboxylic group isn't as serious as
working CH2I2.  Nasty chemical there,
of course SWIM likes H2S and Chloroacetone ...
let the fun begin.

Occassionally an old idea gets brought up in
a new thread and people who haven't seen it
before take a look.
Title: Cinnamic acid to benzaldehyde
Post by: Kinetic on June 07, 2004, 01:22:00 PM
Reducing carboxylic acids to alkanes is rather impractical. How about oxidising 3,4-dihydroxycinnamic acid to protocatechualdehyde with modified permanganate (as ning suggested), followed by methylenation? It may be best to first methylenate to 3,4-methylenedioxycinnamic acid, which would give piperonal directly upon oxidation. The following article deals with the oxidation of plain cinnamic acid to benzaldehyde with permanganate on alumina:

Heterogeneous Permanganate Oxidations. 5. The Preparation of Aldehydes by Oxidative Cleavage of Carbon-Carbon Double Bonds
Donald G. Lee,* Tao Chen, and Zhao Wang
J. Org. Chem. 1993, 58, 2918-2919

(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_imgs/pdf.gif)




Also see

Cleavage of alkenes to aldehydes using potassium permanganate (https://www.thevespiary.org/rhodium/Rhodium/chemistry/alkene2aldehyde.kmno4-thf.html)

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/alkene2aldehyde.kmno4-thf.html).