I am doing an organic chemistry project for school in the form of an acid-base extraction of tolterodine tartrate (Detrol) in ammonium hydroxide (or sodium hydroxide, haven't decided yet) and dissolving the freebase in benzene.

I am planning on crushing up the tablets, and dissolving them in water. Almost all the inactive contents of the tablets are not soluble in water except for lactose monohydrate. Will the presence of lactose monohydrate effect the reaction of the acid base extraction when I add the hydroxide?

  • $\begingroup$ If your intention is to release free base and get it to organic layer, then do not use $\ce{NaOH}$. You may noy able to isolate tolterodine, because of its phenolic moiety. I'd used $\ce{NaHCO3}$ instead. Also, please use toluene in place of benzene. $\endgroup$ – Mathew Mahindaratne Jul 15 at 0:46
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    $\begingroup$ I agree, NaOH is too strong a base and will deprotonate the phenolic -OH.Lactose is highly water-soluble and unlikely to extract into your organic phase. DO NOT USE BENZENE. You should not even have access to benzene $\endgroup$ – Waylander Jul 15 at 6:26
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    $\begingroup$ Thanks for the response. But my question is will the presence of lactose monohydrate in the disolved suspension (along with the detrol) effect the acid base extraction? It shouldnt right? My only question is how lactose monhydrate would potentially impede the free basing process. Im flexible with which solvent ill use. $\endgroup$ – Nader Ganjbaksh Jul 15 at 18:49

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