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Topic: Neutralization of Solketal reaction  (Read 1745 times)

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Offline Delta What?

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Neutralization of Solketal reaction
« on: July 22, 2015, 05:34:21 PM »
Hello this would be my first question asked on the forum so please, if you are willing, give me feedback on the post so I may be able to post with greater ability in the future.

The experiment:
     I am attempting to neutralize a Solketal reaction.
     The reaction steps (abridged)
           Add glycerol, acetone, and H¬2SO4 (catalyst) to a round bottom flask.
           Reflux for an hour
           Cool to room temp
           Neutralize the catalyst with solid (anhydrous/ dried) base.
           Vacuum distill
           Collect Solketal

The observation:
     So I have attempted to use NaOH and Na CO3.  I am noting that it takes quite a while (on the order    of 1 to 2 days) for these bases to neutralize the Sulfuric acid.

The question:
     Why is it taking so long for the bases to react with the catalyst (H2SO4)?
My own thoughts are that the Solketal, excess acetone, or excess glycerol are somehow inhibiting the neutralization reaction. However, I do not know how.

The ultimate question:
     What ideas are out there that I may be able to hasten this neutralization given that I cannot heat the  reaction vessel up and that the bases must be solid (anhydrous/ dried) bases?


Thanks for your help
Hopefullstudent

Offline discodermolide

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Re: Neutralization of Solketal reaction
« Reply #1 on: July 22, 2015, 10:57:56 PM »
Using concentrated sulfuric?
Neutralize with concentrated aqueous base, NaOH, a few drops of 30% should do. Extract product, remove solvent and distill product
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Offline Dan

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Re: Neutralization of Solketal reaction
« Reply #2 on: July 23, 2015, 01:57:09 AM »
The observation:
     So I have attempted to use NaOH and Na CO3.  I am noting that it takes quite a while (on the order    of 1 to 2 days) for these bases to neutralize the Sulfuric acid.

I used to do a lot of acetonide protections and noticed that Na2CO3(s) is extraordinarily slow, but NaHCO3(s) is much faster (you didn't specify which one you used). I don't know if it was solubility, particle size or something else, but I always used to use NaHCO3(s) for this.
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