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Topic: Why is KOH needed in making of phenytoin?  (Read 4424 times)

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Offline redfox

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Why is KOH needed in making of phenytoin?
« on: May 04, 2008, 09:11:23 AM »
Ok, I'm making 5,5'-diphenylhydantoin from benzil and urea and the first steps are to
put them both in a flask and mix with ethanol then add KOH. Why is it important to
use the KOH? Benzil and urea aren't acidic so surely it's not to raise the pH...? That's
about all I know about the use of strong bases so I'm lost for ideas:( Anyone help?

Ta!

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Offline kryptoniitti

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Re: Why is KOH needed in making of phenytoin?
« Reply #1 on: May 04, 2008, 10:35:42 AM »
Look up 'benzilic acid rearrangement'. After you're familiar with it, you should be able to reach the final product with few steps.
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Offline redfox

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Re: Why is KOH needed in making of phenytoin?
« Reply #2 on: May 04, 2008, 10:55:32 AM »
Yeah I've got the full mechanism ta...just need to know why KOH is important...
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Offline kryptoniitti

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Re: Why is KOH needed in making of phenytoin?
« Reply #3 on: May 04, 2008, 11:51:43 AM »
KOH is the source of OH- that attacks the carbonyl and is thus needed to start the rearrangement.
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Offline lutesium

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Re: Why is KOH needed in making of phenytoin?
« Reply #4 on: May 06, 2008, 12:37:43 AM »
It is because of the need to form an enolate.


Lutesium...
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