12diphenylethane12diol

1,2-Diphenylethane-1,2-diol, also known as hydrobenzoin, is an organic compound with the chemical formula C14H14O2. It is a vicinal diol, meaning the two hydroxyl groups are attached to adjacent carbon atoms. This molecule exists as stereoisomers due to the presence of two chiral centers. These include enantiomers of the R,R and S,S forms, as well as the meso compound. The meso form is achiral despite having two chiral centers due to an internal plane of symmetry.

Hydrobenzoin can be synthesized through various methods. One common route involves the reductive coupling of benzaldehyde, often using reagents like magnesium or samarium diiodide. Another approach is the oxidation of stilbene. The physical properties of hydrobenzoin vary depending on its stereoisomeric form, with different melting points and solubilities reported for the enantiomeric and meso forms.

This compound has found applications in organic synthesis as a chiral auxiliary or a precursor for the synthesis of other complex organic molecules. Its ability to form complexes with certain metal ions has also been explored. The study of hydrobenzoin and its derivatives contributes to the broader understanding of stereochemistry and the synthesis of chiral compounds.