Crystallization features and spontaneous resolution of 3-(2,6-dimethoxyphenoxy)propane-1,2-diol: The case of stable conglomerate and metastable solid solution

Phase behavior of 3-(2,6-dimethoxyphenoxy)propane-1,2-diol 1 was investigated by IR spectroscopy, X-ray diffraction, and DSC methods. Racemic diol 1 prone to spontaneous resolution and has been resolved into (S)- and (R)-enantiomers by a preferential crystallization procedure. Separation takes place, but it gives crystalline precipitates with moderate (60–70%) enantiomeric excess values. The plausible reason is the formation of metastable phase of solid solution during the crystallization.