rac-2-[(2-Chlorophenyl)(4-chlorophenyl)methyl]-1,3-dioxolane

Abstract

The title compound, C16H14Cl2O2, is a chiral mitotane derivative that contains a dioxolane ring and crystallizes from methanol as a racemic mixture. It was obtained in high yield from mitotane and ethyleneglycol in alkaline medium, followed by neutralization with sulfuric acid and extraction with ethyl acetate. The molecular structure is stabilized by an intramolecular C— H... O hydrogen bond. The dihedral angle between the aromatic rings is 80.1 (2)°. The dioxolane ring adopts a puckered envelope conformation with an O atom as the flap.