The Phase Behavior and Crystallization of 2-Chloromandelic Acid: The Crystal Structure of the Pure Enantiomer and the Behavior of Its Metastable Conglomerate

Crystallization of racemic 2-chloromandelic acid yields a metastable conglomerate in addition to a more stable racemic compound. The crystal structure of the pure enantiomer is reported and the relative stability of the racemic compound and conglomerate was determined at both room temperature and the melting point. Crystallizations from melt and solution are shown to offer potential crystallization pathways to the conglomerate, provided crystallization of the racemic compound can be avoided.