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Alcohols to carbonyls w/ peracetic, ethyl acetate, NaBr
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methyl_ethyl
Riedel De Haen
Joined: 18 Feb 2005
Posts: 107
Location: Estonia
7200.76 Points

Tue Feb 22, 2005 10:26 am
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Not sure where I found this, Unfortunately I can not give credit to the person that posted this, I think I would remember if I found this on my own, regardless here is a related article, I apologize in advance if this has already been posted at Synthetika.

Oxidation of alcohols with peracetic acid in ethyl acetate in the presence of Sodium Bromide
Takashi Morimoto, Masao Hirano, Takayoshi Hamaguchi, Masahide Shimoyama, and Xiumin Zhuang
Bull. Chem Sc. Jpn, 65, 703-706 (1992)
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Abstract:

Aliphatic primary alcohols and 1,x-diols were oxidized to the dimeric esters and lactones, respectively, by peracetic acid and ethyl acetate in the presence of sodium bromide under mild conditions. Aliphatic secondary and benzylic alcohols were converted smoothly to the corresponding carbonyl compounds by the same system.
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exhive

Joined: 09 May 2005
Posts: 1
Location: Central Europe
30.26 Points

Mon May 09, 2005 1:34 pm
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Didn't have time to look at this article, but I suppose this is a variation on Br2/H2O2 theme. Always wondered why anyone would pursue this route when you can (almost) always use acidic aq NaOCl/Ca(OCl)2 with excellent results (known not only from theory, hehe).
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IndoleAmine
Dreamreader Deluxe
Joined: 09 Feb 2005
Posts: 681
Location: Bahamas
18717.10 Points

Tue May 10, 2005 6:51 am
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its because of the "almost" - the reason why its nice to have several different procedures at hand for each transformation....
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