Extraction for mixture of alcohol acid amine ketone

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Madformedic
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Hi all, I only know that I can add NaOH to then HCL to separate the acid, but then I am left with a layer with a mixture of amine ketone and alcohol which are all polar and soluble in water, anyone can suggest how I can continue extract them out?
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scimus63
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I think your alcohol is a substituted phenol not an alcohol!

Not sure just guessing here but:
for the ketone you can precipitate out a crystalline derivative by dissolving in methanol and adding 2.4 DNP. Then simply filter out the solid.
For the amine could you add copper sulfate solution and also produce a solid precipitate? Or simply precipitate out the tertiary ammonium salt and then filter
For the phenol derivative I would add sodium hydroxide to produce the phenoxide ion which will not dissolve in the ether I think, then add conc HCl to precipitate out the phenol derivative.
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