ORGLIST:Separation of Organic Compound from Aqueous Solution

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From: researchstuff$##$bellsouth.net
Date: Tue Nov 04 2003 - 00:01:45 EST

Hello All:

   I think I have made a 4-fluorobenzamidine derivative, more specifically, N'hydroxy,N'methyl-4-fluorobenzamidine. The problem is that I can't extract it from the aqueous phase. I am thinking the hydroxy and fluoride moieties of the amidine are hydrogen bonding with water, thus enhancing its aqueous solubility. Aqueous work-up is necessary for the separation because another salt (KCl)and t-butyl alcohol are produced in the reaction and need to be isolated from the product. I have tried extractions with the usual solvents: CH2Cl2 and ethyl acetate. A TLC of the aqueous phase shows the presence of an organic compound.

   Well, in an case, has anyone ever extracted aqueous soluble organic compounds? Or know of a reference to this type of extraction.

   By the way, if this helps, I am running the reaction in methanol. I am reacting 4-fluorobenzonitrile, methylhydroxyamine-HCl and tBuOK. For the work-up: the solvent is evaporated, water added, followed by extraction with the organic solvents mentioned above.

 Thanks for any guidance here.
  
Mark

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