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Author: Subject: Oxidation of 2-octanol or 2-octanone to hexanoic acid
vinda
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[*] posted on 13-11-2013 at 03:29
Oxidation of 2-octanol or 2-octanone to hexanoic acid


Dear all
I am trying on air / aerobic oxidation of Oxidation of 2-octanol or 2-octanone to hexanoic acid without using nitric acid.

do you have suggestions
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bbartlog
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[*] posted on 13-11-2013 at 05:45


How would that even work? Assuming you cleave the final carbon and oxidize the remaining chain (via the haloform reaction, maybe), you still have heptanoic acid, which is one carbon atom longer than what you're aiming for.



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blogfast25
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[*] posted on 13-11-2013 at 06:01


Can't work, belongs in organics section.



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Nicodem
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13-11-2013 at 07:01
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[*] posted on 13-11-2013 at 07:06


Quote: Originally posted by blogfast25  
Can't work, belongs in organics section.

I cannot say it can work because I did not bother checking the literature, but it might work by the Willgerodt-Kindler reaction followed by the thioamide hydrolysis. There are other ways, but none is really practical, certainly not for something so simple and cheap.

PS: Vinda, please read the forum guidelines. Threads opened without any reference belong to the Beginnings section.




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[*] posted on 9-1-2014 at 05:34


Air is not a sufficiently powerful oxidising agent to oxidise a ketone to a carboxylic acid. You would need a much, much more powerful oxidising agent.
In order to convert the heptanoic acid formed into hexanoic, you could to a Hofmann reduction.




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