hydride_shift
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butanoic acid from sandmeyer rxn
So butanoic acid is a smelly smelly thing which happens to be produced following a GABA -> diazonium intermediate (the specifics of which are well
documented).
What interests me is the possibility of salvaging waste butanoic acid from such a reaction for the preparation of low-molecular-weight esters of
butyric acid.
Better yet, what conditions would favour the formation of butanoic acid as opposed to the lactone?
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kch
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I would say that since the lactone hydrolyzes to the acid, a little water would be more favorable
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turd
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I think you misunderstood OPs question.
I think OP's talking about this reaction: http://www.erowid.org/archive/rhodium/chemistry/gaba2ghb.htm... (shame on you for not providing the link) and the presumable butyric acid side
product. Since it is probably only a minor side product the question is a bit silly.
Or maybe it's me who misunderstood the question - it was not asked in a very coherent way (confusion of lactone and gamma-hydroxy-acid?) had no
references and is a classic example of how-not-to-post.
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bfesser
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Thread Moved
19-8-2013 at 14:29 |
kch
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Quote: Originally posted by turd  | I think you misunderstood OPs question.
I think OP's talking about this reaction: http://www.erowid.org/archive/rhodium/chemistry/gaba2ghb.htm... (shame on you for not providing the link) and the presumable butyric acid side
product. Since it is probably only a minor side product the question is a bit silly.
Or maybe it's me who misunderstood the question - it was not asked in a very coherent way (confusion of lactone and gamma-hydroxy-acid?) had no
references and is a classic example of how-not-to-post. |
I think I misunderstood the butanoic acid part, but I think I'm right about the lactone to acid
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hydride_shift
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I apologize for any misunderstanding/not referencing said article, and perhaps a poor first thread post. I simply did not want seem to have the wrong
intentions.
After attempting said reaction, a long arduous distillation was performed at 120*C, in which (what i presumed was) the majority of lactone in
azeotrope was removed. Left in the boiling flask was about 50mL of a VERY stinky solution, which began to precipitate white crystals (presumably
unreacted gaba/butaonic acid salts?).
The solution had a pH ~7 and is shown bellow
<img src="http://imageshack.us/scaled/thumb/812/0hf1.jpg">
I was wondering if there was any merit in attempting to salvage Butanoic acid aka butyric acid (CH3CH2CH2-COOH) from said solution for the benign
purposes of turning this rancid smelling compound into a sweet smelling one via esterification.
I was considering a simple distillation at ~165*C, or perhaps even drying the precipitate and reacting with a strong acid to see what i got,
Any thoughts on this?
[Edited on 21-8-2013 by hydride_shift]
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I Like Dots
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Try to remove all the GHB/GBL with more water and distillation. Distilling seems the easiest.
Why not an acid base extraction? Butyric acid has a pKa of 4.82
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