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Topic: Hydrolysis Work-up  (Read 3392 times)

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Offline AlphaScent

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Hydrolysis Work-up
« on: October 18, 2012, 11:26:44 AM »
A hydrolysis of an acetate done in with 10% NaOH in Methanol.  The work up says to wash with 1 N HCl.  I say to extract my product with hexanes and then wash.  What do you think?
If you're not part of the solution, then you're part of the precipitate

Offline discodermolide

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Re: Hydrolysis Work-up
« Reply #1 on: October 18, 2012, 11:42:26 AM »
Wash it with acid first then extract, methanol/water and hexane don't mix.
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Offline sjb

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Re: Hydrolysis Work-up
« Reply #2 on: October 18, 2012, 11:43:06 AM »
A hydrolysis of an acetate done in with 10% NaOH in Methanol.  The work up says to wash with 1 N HCl.  I say to extract my product with hexanes and then wash.  What do you think?

Why do you think the work-up is described as given? How will things be affected with your work-up?

Offline AlphaScent

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Re: Hydrolysis Work-up
« Reply #3 on: October 18, 2012, 12:04:49 PM »
I have done this reaction on similar compound except this has one double bond, where the other was a diene.  What I did before was extract then wash, 99% yield.  I thought it odd the procedure given to me from a grad thesis was opposite.  I am going to wash first with 1 N HCl.  Ill post results in a few hours... Wash with 1 N HCl until acidic, extract with hexanes..wash with brine, filter and remove solvent i.v....should be great...
If you're not part of the solution, then you're part of the precipitate

Offline cvrlik

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Re: Hydrolysis Work-up
« Reply #4 on: October 22, 2012, 09:55:26 AM »
A hydrolysis of an acetate done in with 10% NaOH in Methanol.  The work up says to wash with 1 N HCl.  I say to extract my product with hexanes and then wash.  What do you think?
I thing you need to add HCl first because Na-salt is not soluble in hexane...

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