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Topic: Preparation of Diphenhydramine  (Read 8717 times)

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l_ame

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Preparation of Diphenhydramine
« on: June 04, 2005, 09:58:30 AM »
Hello, I'm sure this is extremely simple, but I'm supposed to draw the mechanism for this reaction. Can anyone start me off by telling me what kind of reaction this is in the first place, please? thanks!
« Last Edit: June 04, 2005, 10:02:34 AM by l_ame »
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l_ame

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Re:Preparation of Diphenhydramine
« Reply #1 on: June 04, 2005, 10:11:43 AM »
... is it a Williamson Ether Synthesis?  ???
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Re:Preparation of Diphenhydramine
« Reply #2 on: June 05, 2005, 12:50:20 PM »
Quote from: l_ame on June 04, 2005, 10:11:43 AM
... is it a Williamson Ether Synthesis?  ???

Looks like it to me.

There are two mechanism you have to consider though.  It may be difficult to tell which one is actually operating here.
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dexangeles

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Re:Preparation of Diphenhydramine
« Reply #3 on: June 06, 2005, 04:57:34 AM »
Quote from: l_ame on June 04, 2005, 10:11:43 AM
... is it a Williamson Ether Synthesis?  ???

well you have to have a base first for it to be a Williamson Synthesis
so, my best bet is that the CO3 deprotonates the OH to form your base
then it should be SN2 after that
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