2-hydroxymethyl-1,4-dioxane: Synthesis, resolution and determination of the absolute configurations of the enantiomers

2-Hydroxymethyl-1, 4-dioxane 3 was resolved via salt formation between its hydrogen phthalate and (R)- or (S)-1-phenylethylamine, selective crystalliz ation of the resultant diastereomeric mixtures and subsequent recovery of i ts enantiomers by saponification. The progress! of the resolution was follo wed by chiral HPLC and the absolute stereochemistry of the two enantiomers determined by comparison of their specific rotations with that of (R)-3 syn thesized from enantiomerically pure (R)-1-O-benzylglycerol. The results of the synthesis of 3 and of its resolution are discussed and compared with th ose previously obtained for 1,2-isopropylidene glycerol evaluating the cons equences of replacement of ispropylidene with an ethylene bridge.