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Molecularly imprinted microspheres (MIMs) of D-mandelic acid were synthesized in this study. Chloromethylated polystyrene beads modified with iniferter were used as supports for photo-grafting of a molecularly imprinted polymer (MIP) layer. The polymers were characterized by FT-IR, elemental analysis and thermo-gravimetric analysis to testify the polymer formation and its thermal stability. Scanning electron micrographs (SEM) show that the MIP particles are mono-dispersed and well-spherical, with the average diameter of 4.38 μm and size distribution coefficient of 1.02. Furthermore, the MIMs were packed in a stainless steel column and evaluated as stationary phases in high performance liquid chromatography (HPLC). The prepared MIP exhibited a considerable capability of chiral separation between template and its enantiomer. Accordingly, this kind of MIP is likely to have wide applications in chemical sensing, chromatographic analysis and solid phase extraction.