I have an amino carboxylic acid that is practically insoluble in most alcohols and in water, but supposedly soluble in an 20% NaOH solution. A basic reaction is run with an organic solvent/reactant, and the amino carboxylic acid dissolved in the NaOH solution. After the reaction the layers are easily separated. With the NaOH layer separate, by what method is the carboxylic acid able to be extracted from the NaOH layer? I've read one way to do this is to neutralize the base with equal parts Hydrochloric acid but I am unsure if the carboxylic acid will dissolve in HCL, and if possible, I would want to avoid such acids all together. Any ideas?