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Topic: feist-benary synthesis?  (Read 9034 times)

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Offline vices7070

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feist-benary synthesis?
« on: February 28, 2007, 10:21:25 PM »
Please see the attached image for the reaction.  I'm not sure how to display the file here.



I've been trying to see what compounds this will create.  I am unable to deduce the name of the reactant, which makes searching for the type of reaction harder.

I tried looking up furan instead as that is a similar type of product that could occur, which lead me to the Feist-Benary synthesis.  The key difference seems to be that the standard C=O bond is missing, and in its place we have a S=O bond. 

I also tried to look up hemiacetal and acetal formation, as the book makes reference to them.  Unfortunately I wasn't able to find any relevant information.

From Glucose hemiacetal formation I understand that a C=O bond can break, and a hydroxyl carbon from further down the chain will bond with the O, making a furan-type bond.  (Name?)

I'm really not sure where to go from here.  If someone either knows the mechanism or the reaction or how to find them I would appreciate that info very much. :)


This is my first post on this forum and I look forward to exciting chemistry discussion. ;)


Thanks!

Offline Custos

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Re: feist-benary synthesis?
« Reply #1 on: February 28, 2007, 11:44:42 PM »
The compound is called glutaric acid.

Sulphuric acid is a powerful dehydrating agent. Dicarboxylic acids are prone to formal dehydration (loss of the elements of water) to give anhydrides. Perhaps that's what you are looking for?

Offline movies

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Re: feist-benary synthesis?
« Reply #2 on: March 01, 2007, 02:12:41 AM »
The Feist-Benary synthesis is different.  It makes furans.  You have too many carbons for that!


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