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Author: Subject: Epoxidation of propiophenone
Crypto
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[*] posted on 1-6-2014 at 23:57
Epoxidation of propiophenone


Hi!

I stumbled on a nice method for the preparation of styrene oxide posted by Nicodem some time ago:

http://www.sciencemadness.org/talk/viewthread.php?tid=15284#...

I was thinking if it would work on other compounds. I have about 50g of propiophenone and would love to try, but the only thing that holds me back is that I'm not sure if it will acctually work and I don't want to waste what I've got, because I haven't got a lot of it.

I know that the epoxide can be prepared by bromination, reduction with NaBH4 and treating with KOH. I don't have any borohydride thou and it's pretty expensive and hard to get at my end. The method posted by Nicodem is simple and uses common chemicals.
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sparkgap
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[*] posted on 2-6-2014 at 03:00


If you look at the structure of propiophenone, you should be able to notice the lack of features similar to that of styrene that can be epoxidized. In particular, note the lack of C=C bonds in your ketone.

The nearest thing you can do to convert your ketone to an epoxide is Corey-Chaykovsky, yet this is certainly not something that can be easily done outside a professional lab.

sparky (~_~)




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Paddywhacker
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[*] posted on 2-6-2014 at 20:48


What about the enol form, sparkgap?
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Nicodem
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[*] posted on 2-6-2014 at 22:34


Quote: Originally posted by Paddywhacker  
What about the enol form, sparkgap?

The epoxidation of enols or ionic enolates does not give an epoxide, but it gives alpha-hydroxyketones. For this reason it is not commonly referred to as an epoxidation. In the literature it is commonly called alpha-hydroxylation of ketones and uses rather specific reagents (often oxygen in conjunction with a base, aryliodoso reagents, etc.). Obviously, the epoxidation cited by Crypto is not suitable to do this transformation.




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[*] posted on 3-6-2014 at 00:32


Thank you all. I still need to learn a lot... I thought I'll finaly use the propiophenone for something because I have it for some time now, and don't have any idea what to do with it ;) I was thinking about it's reduction to alcohol but NaBH4 is out of my reach. I read one could use sodium dithionite for the reduction, but the procedure is not that great (lots of dithionite and solvent needed).

Anyway thanks :)
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[*] posted on 4-6-2014 at 06:41


With respect to the reduction, you might consider using thiourea dioxide for the purpose. Have you seen this?

sparky (~_~)

[Edited on 4-6-2014 by sparkgap]




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