06-06-04 20:11
No 511810
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':
I first read about it here:
http://www.fslemi.uni-bonn.de/gewuerze/h
References are here http://www.paracelsus.de/heilv/natur_177
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?
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 (../rhodium /methyl
The moving of the double bond can of course be found here (../rhodium /isomer
I don't have the knowledge to answer this question yet, hope you can help.
This is the ant, my only friend the ant
(Hive Bee)
06-06-04 21:01
No 511812
caffeic acid.
http://www.mikuriya.com/mmp.html
(Stranger)
06-06-04 21:22
No 511815
Ahaaaaa!
Thanks
It's fun though, putting the pieces together for myself, a great learning experience!
This is the ant, my only friend the ant
(acetaminophanatic)
06-06-04 21:58
No 511819
Perhaps we at the hive would have a use for some 3,4-dihydroxybenzaldehyde....?
Ozone, or perhaps KMnO4 under certain conditions?
We'll all meet someday...on the other side
(Active Asperger Archivist)
06-06-04 21:59
No 511820
do a search:
Post 122772 (dormouse: "MDA from Coffee -Wizard X", Serious Chemistry)
Post 323392 (mellow: "MDP2P from waste vegetation?", Novel Discourse)
Act quickly or not at all.
(Hive Bee)
06-07-04 00:04
No 511839
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? :-)
(Hive Bee)
06-07-04 10:17
No 511911
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.
(Hive Bee)
06-07-04 13:22
No 511939
(Rated as: excellent)
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
Also see Cleavage of alkenes to aldehydes using potassium permanganate (../rhodium /alkene