Sciencemadness Discussion Board

Aromatic to Cyclohexane compound

enkay - 21-8-2006 at 09:15

Hey friends !

Is it possible to make :

4-Aminomethyl Cyclohexane Carboxylic acid FROM 4-Aminomethyl Benzoic acid....?


No such data in beilstein available for this route. Can anyone pls help me out for this ?

[Edited on 21-8-2006 by enkay]

4-Aminomethyl Cyclohexane Carboxylic acid.gif - 356B

samdar - 21-8-2006 at 17:27

no, most reagents/ reaction conditions that will reduce the benene ring(ie. raney nickel or pd carbon under pressure) will destroy your functionality.

ergoamide - 21-8-2006 at 22:44

Hmm you could try a birch reduction maybe to get it to a diene and form there not sure how ya might gop about reducing the other double bonds, maybe NaBH4 but i aint sure.

not_important - 22-8-2006 at 00:50

Well, http://www.pubmedcentral.gov/articlerender.fcgi?artid=93338 says
Quote:
The anaerobic bacterium Syntrophus aciditrophicus metabolized benzoate in pure culture in the absence of hydrogen-utilizing partners or terminal electron acceptors. The pure culture of S. aciditrophicus produced approximately 0.5 mol of cyclohexane carboxylate and 1.5 mol of acetate per mol of benzoate


The start of an article using platinum and haloacid, you'll need to get the full article to see if it works for you
http://pubs.acs.org/cgi-bin/abstract.cgi/jacsat/1936/58/i09/...

ziqquratu - 22-8-2006 at 02:28

Article attached:

J. H. Brown, H. W. Durand, and C. S. Marvel (1936) "The Reduction of Aromatic Compounds with Hydrogen and a Platinum Oxide- Platinum Black Catalyst in the Presence of Halogen Acid", J. Am. Chem. Soc, 58(9), 1594 - 1596

Attachment: Aromatic Reduction with Pd+HX.pdf (316kB)
This file has been downloaded 1199 times

not_important - 22-8-2006 at 09:58

Ah, thank you ziqquratu! Not only does that look as if would be useful to enkay, it might do the trick when one needs a small amount of some cycloalkanes. It also appears that short reaction times could be used to remove a halogen from an aromatic, although you'd probably want to recycle unreacted material.