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Topic: Synthetic problem: Hydrolysis of esters upon neutralization  (Read 2123 times)

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Offline JSUCY232

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Synthetic problem: Hydrolysis of esters upon neutralization
« on: December 16, 2013, 09:14:15 PM »
I have been working on synthesizing some esters from alcohols and acids. (Esters of phthalic acid) I can synthesize them, but upon neutralization, the esters always hydrolyse. This occurs quickly, such that the starting acid (which is a solid) precipitates immediately in aqueous solution. I have neutralized them before performing a water extraction (in the presence of alcohol), but the problem is that if the solution is not exactly neutral, the esters hydrolyse because the acid makes such a stable leaving group. These esters are commercially available, so I don't see why I'm having so much trouble synthesizing them.  ??? Any help would be appreciated.

Offline discodermolide

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Re: Synthetic problem: Hydrolysis of esters upon neutralization
« Reply #1 on: December 17, 2013, 02:34:57 AM »
If you can tell us the reaction conditions you are using it may help pinpoint the problem.
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