I have been working on synthesizing some esters from alcohols and acids. (Esters of phthalic acid) I can synthesize them, but upon neutralization, the esters always hydrolyse. This occurs quickly, such that the starting acid (which is a solid) precipitates immediately in aqueous solution. I have neutralized them before performing a water extraction (in the presence of alcohol), but the problem is that if the solution is not exactly neutral, the esters hydrolyse because the acid makes such a stable leaving group. These esters are commercially available, so I don't see why I'm having so much trouble synthesizing them.
Any help would be appreciated.