Diastereomeric resolution of p-chloromandelic acid with (R)-phenylethylamine.

The optical resolution of p-chloromandelic acid using (R)-alpha-phenylethylamine as resolving agent was presented. The effect of solvents, molar ratio of racemate to the resolving agent, filtration temperature as well as the amount of solvent on resolution was investigated by orthogonal experimentation. The binary melting point phase diagram and crystal structure analysis of diastereomeric salts rationalized the success of the resolution. Copyright 2009 Wiley-Liss, Inc.