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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: mir on March 19, 2006, 02:40:17 PM

Title: Workup: removing acetic acid
Post by: mir on March 19, 2006, 02:40:17 PM

I have a mixture of an highly activated phenol, acetic acid in ethyl acetate (20 mL). I have already removed most of the substrates. But how do I remove the acetic acid?

I tried washing the mixture with water, with no success. The mixture still contained much acetic acid, which was apperent as a strong smell after using the rotavapor. Im using wateraspirator to lower the pressure inside the rotavapor, so evaporating the acid is not possible without strong heating.

Any suggestions?

Title: Re:Workup: removing acetic acid
Post by: Yggdrasil on March 19, 2006, 05:15:55 PM

Try washing with aqueous sodium bicarbonate.  The bicarbonate is a strong enough base to deprotonate the acetic acid and make it more water soluble, but it won't deprotonate the phenol, so the phenol will stay in the organic layer.