Spontaneous Enantiomeric Resolution of 1,3-Diols from the Naphtylidene Derivative of 2,4-Pentanedione

Enantiomers (2S, 4S)- and (2R, 4R)-3-(naphthalene-1-ylmethyl) pentane-2,4-diols were synthesized by the reduction of (Z)-4-hydroxy-3-(naphthalene-1-ylmethyl) pent-3-en-2-one with NaBH4 in methanol (MeOH). Crystallization dichloromethane this racemic mixture led to simple crystals a crystalline habit similar morphologies; however, group them, it was possible find barely observable difference that allowed determining crystal structure for each enantiomers, 2S,4S, 2R,4R.