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Topic: methylendioxy group treated with H+/H2O  (Read 1741 times)

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Offline Bakterien

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methylendioxy group treated with H+/H2O
« on: June 25, 2014, 02:18:45 PM »
The molecule was a benzene with a methylendioxygroup (just like MDMA). What will happen if I treat it with H+/H2O? I think that the methylenedioxy group will be cleaved to the corresponding diol. Is that correct? But if that is true how come MDMA can be taken orally? The acidic enviorment in the stomac will break the methylendioxy bride and the drug give effect.

Or is MDMA a prodrug?
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Offline TheUnassuming

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Re: methylendioxy group treated with H+/H2O
« Reply #1 on: June 25, 2014, 05:55:02 PM »
Generally you would be hard pressed to cleave that dioxole moiety with simple protic acid.
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When in doubt, avoid the Stille coupling.

Offline zsinger

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Re: methylendioxy group treated with H+/H2O
« Reply #2 on: July 01, 2014, 02:47:32 PM »
Need something like AlCl3 I believe!
              -Zack
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"The answer is of zero significance if one cannot distinctly arrive at said place with an explanation"
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