Abstract

Dihydrobenzoin was synthesized by a reaction of benzoin and sodium borohydride. The

resulting diol was then converted to 2,2-dimethyl-4,5-diphenyl-1,3-dioxolane using acetone and
FeCl3. This was followed by recrystallization of the acetal. The 1H and 13C NMR showed that the
acetal present was in fact the meso form. This was shown due to the appearance of only one
peak (1.8ppm) corresponding to the methyl groups in the acetal. The IR spectrum shows only a
single sharp peak (1454 cm-1) that corresponds to the methyl groups of the acetal. The
appearance of single peaks in both these areas shows that the stereoisomer formed was the
meso acetal.

Conclusion

Dihydrobenzion was successfully synthesized in a miniscule yield. The IR and melting point data
was consistent with the expected data. Lee’s much larger dihydrobenzoin sample was
converted to the acetal using anhydrous acetone and FeCl3. The spectra showed peaks specific
to the presence of a symmetric stereoisomer through the appearance of a single peak shown
for the two present methyl groups. This data was consistent with the expected data and would
suggest the meso stereoisomer is the product of the reaction.