I need to separate these 4 by extraction, I don’t work in a lab but I was wondering if this way would be possible. First I’d use a weak base to ionize the carboxylic acid to make it go to the aqueous phase and separate , then use a strong base to ionize the phenol and separate, but I’m left with two that I don’t know what to do (using extraction by solvents not form complexes) , how would I separate them? If I use a strong acid to ionize methylpyridine then it would also hydrolyze the ester.
Any ideas? Ty