Separation of 1,1 '-binaphthalene-2,2 '-diol optical isomers by derivatization high performance liquid chromatography
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1, 1'-Binaphthalene-2,2'-diol-mono-[(-)-menthyl] carbonate (3) and 1, 1'-binaphthalene-2, 2'-diol-bis- [(-)-menthyl] carbonate (4) are intermediates in the chemical resolution of racemic 1, 1'-binaphthalene-2,2'-diols (1) utilizing (-)-(1R)-menthyl chloroformate (2) as the derivating agent. In this paper, the optical separation of compound (3) and (4) has been investigated by high performance liquid chromatography on Lichrosorb Si-60(4 mm i. d. x 300 mm, 5 mum) and YWG-CN (4 mm i. d. x 250 mm, 10 mum) column with hexane-polar regulator mixture as an eluent. The results show that the optical isomers of compound (3) and (4) can be wen separated. The optical isomers first eluted are (S, 1R')-3 and (S, 1R', 1R ")-4 respectively. The influence of polar solvents and their ratios in the mobile phase on the resolution is examined. This method has been applied to determine the optical purity of 1, 1'-binaphthalene-2,2'-diol-mono-[(-)-menthyl] carbonate obtained from a novel resolution process.