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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Bakterien on June 25, 2014, 02:18:45 PM

Title: methylendioxy group treated with H+/H2O
Post by: Bakterien 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?

Title: Re: methylendioxy group treated with H+/H2O
Post by: TheUnassuming on June 25, 2014, 05:55:02 PM

Generally you would be hard pressed to cleave that dioxole moiety with simple protic acid.

Title: Re: methylendioxy group treated with H+/H2O
Post by: zsinger on July 01, 2014, 02:47:32 PM

Need something like AlCl3 I believe!
              -Zack