A convenient preparation of enantiopure 1,1′-bi-2-naphtholsvia an inclusion complexation in the solid state

Abstract

Inclusion reaction of racemic 1,1′-bi-2-naphthol and (S)-proline was examined under the solid state and the solid-liquid conditions. The results indicated that a solid mixture of racemic 1,1′-bi-2-naphthol and (S)-proline in a 1∶1 molar ratio was kept at 50–80 °C for 3–4 h, followed by treatment with benzene to give an insoluble solid and a benzene solution, from which (S)-(−)- and (R)-(+)-1,1′-bi-2-naphthols of a modest level of optical purity were obtained. After “kinetic” crystallization, both essentially enantiopure isomers were provided in 15%–35% overall yields, respectively.