Aqua-regia
Hazard to Others
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 126
Registered: 18-12-2006
Member Is Offline
Mood: No Mood
|
|
Help for preparation of 2 benzylpyridine
2-benzylpyridine is a starting material for 2-(2,4-dinitrophenyl)pyridine. This is an interesting photochromic compound
http://courses.chem.psu.edu/chem36/Chem36H/IndivExpt1/440%20...
Can somebody tell my a way to obtain 2-benzylpyridinel from benzene + AlCl3 and suitable pyridinederivate
thanks!!
|
|
Chordate
Hazard to Others
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 108
Registered: 23-2-2011
Member Is Offline
Mood: No Mood
|
|
What do you mean by suitable pyridine derivate? Choose a reaction scheme and then acquire the chemicals, not the other way around.
|
|
Dr.Bob
International Hazard
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 2690
Registered: 26-1-2011
Location: USA - NC
Member Is Offline
Mood: No Mood
|
|
I can't understand a university lab naming the compound wrong, but the product would be 2-(2,4-dinitrobenzyl)pyridine, since the methylene group is
still present. I would look at the J Chem Ed for the reference to the preparation of the SM. It will likely be there.
The simplest pyridine SM I have used is 2-chloropyridine, but I don't know if it would react with a benzyl halide or benzyl organometallic directly.
You might be able to acylate benzene with 2-pyridinoyl chloride and then reduce the ketone away. I don't think 2-chloromethylpyridine would react
with benzene in a Friedel Craft reaction, but you could look it up to see.
Bob
|
|
Aqua-regia
Hazard to Others
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 126
Registered: 18-12-2006
Member Is Offline
Mood: No Mood
|
|
Hi Dr Bob and Chordate
I founded this patent , there is a reaction sheme but the matter is unfortunatelly in japanese language:
http://worldwide.espacenet.com/publicationDetails/biblio?DB=...
This is the next usable article, but I dont have access
http://pubs.acs.org/doi/abs/10.1021/ja01181a506
|
|
ScienceSquirrel
International Hazard
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 1863
Registered: 18-6-2008
Location: Brittany
Member Is Offline
Mood: Dogs are pets but cats are little furry humans with four feet and self determination!
|
|
It looks like the patent details the reaction of chloromethylpyridine with benzene in the presence of aluminium chloride. I would expect this to be a
fairly straight forward Friedel Crafts reaction.
|
|
Aqua-regia
Hazard to Others
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 126
Registered: 18-12-2006
Member Is Offline
Mood: No Mood
|
|
Yes i realized, but is a hard way again. Not easy to get syntetically 2-chloromethylpiridine in home lab.
|
|
DJF90
International Hazard
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 2266
Registered: 15-12-2007
Location: At the bench
Member Is Offline
Mood: No Mood
|
|
If you U2U me an email address I'll send you a couple papers for making the 2-benzylpyridine using compounds/reagents you should be able to get/make.
If you're in the UK I might also be able to help you on that front also.
|
|
Dr.Bob
International Hazard
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 2690
Registered: 26-1-2011
Location: USA - NC
Member Is Offline
Mood: No Mood
|
|
Look at the following to see the entire paper in JACS. It uses pyridine and benzyl chloride as the main reagents and copper as the catalyst. Those
are about as simple of reagents that you could ask for. That is a pretty interesting way to do it.
See the links below to see the last 2 pages of the article. (or just hit the next button on the link above).
http://pubs.acs.org/doi/abs/10.1021/ja01181a507
http://pubs.acs.org/doi/abs/10.1021/ja01181a508
|
|
Aqua-regia
Hazard to Others
![*](images/xpblue/star.gif) ![*](images/xpblue/star.gif)
Posts: 126
Registered: 18-12-2006
Member Is Offline
Mood: No Mood
|
|
My referred paper above (http://pubs.acs.org/doi/abs/10.1021/ja01181a506) is the same. Thank you, it is really usable way. Disadvantage of this methode is the niggling
of isomers.
|
|