Author Topic: major side product in performic acid oxidation?  (Read 107 times)

akcom

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major side product in performic acid oxidation?
« on: March 07, 2013, 02:53:09 AM »
Hi all, this is a cross post from another forum so forgive me if you've seen this already.  Hoping to get some input on the situation.

A buffered performic acid synthesis of MDP2P was performed in DCM on a small amount of isosafrole.  The reaction was worked up per the literature except HCl was used instead of H2SO4 to form the ketone.  After distillation, two products were noted on TLC (5% EtOAc in Toluene).   The spots have a very similar RF.  The primary spot (MDP2P) is about RF .54 with the major side product being around 0.58.

Separation by column chromotography was fruitless due to the very similar RF values.  Judging by the intensity of the spot under UV light there is a fair amount of whatever this stuff is.  Is this likely MDP1P?  I'm very hesitant to put this through a mass spec, but my curiosity may get the best of me.

I'd love to here any thoughts on likely side products.  The smell and color are spot on.  The only thing I can come up with is MDP1P

ImAMANGUYS

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Re: major side product in performic acid oxidation?
« Reply #1 on: March 07, 2013, 05:21:57 PM »
hxxp://www.sciencedirect.com/science/article/pii/S0379073808001746

Hope this helps  ;D

Don't know if you can find anything you need? But perhaps it would be helpful in your search if noone else has any ideas.

akcom

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Re: major side product in performic acid oxidation?
« Reply #2 on: March 07, 2013, 06:59:58 PM »
Very helpful! Thank you much

RoidRage

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Re: major side product in performic acid oxidation?
« Reply #3 on: March 08, 2013, 02:40:17 AM »
hxxp://www.sciencedirect.com/science/article/pii/S0379073808001746

Hope this helps  ;D

Don't know if you can find anything you need? But perhaps it would be helpful in your search if noone else has any ideas.

Here is the full cited paper

Chemical markers from the peracid oxidation of isosafrole
M. Coxa,G. Klassb, S. Moreyb, P. Pigoua
Forensic Science International
Volume 179, Issue 1, 18 July 2008, Pages 44–53
DOI: 10.1016/j.forsciint.2008.04.009


pbinteger

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Re: major side product in performic acid oxidation?
« Reply #4 on: March 08, 2013, 03:37:07 AM »
Excellent! I was curious as to the specific impurities produced in side reactions and their ratios. Thank you for running that analysis akcom and thanks for the ref(s) IMA and Roid....



ImAMANGUYS

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Re: major side product in performic acid oxidation?
« Reply #5 on: March 08, 2013, 05:55:34 AM »
I'd say you're welcome but it looks like Roid one up-ed me  :o

Thanks Roid :P  8)

akcom

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Re: major side product in performic acid oxidation?
« Reply #6 on: March 08, 2013, 04:08:32 PM »
Whatever this compound is it does not undergo reductive amination so is not, ultimately, a concern as long as proper A/B work up is done.