4777. Hydrobenzoin

Nomenclature

CAS number: 492-70-6
1,2-Diphenyl-1,2-ethanediol; diphenylethyleneglycol.
C14H14O2; mol wt 214.26.
C 78.48%, H 6.59%, O 14.93%.

Description and references

Prepn of d-, l-, dl- and meso-forms: Forst, Zincke, Ann. 182, 262, 275 (1876); Irvine, Weir, J. Chem. Soc. 91, 1390 (1907); Buck, Jenkins, J. Am. Chem. Soc. 51, 2163 (1929); L. F. Fieser, Organic Experiments (D. C. Heath, Boston, 1964) pp 210, 214, 216-217, 229-231. Improved method for prepn of dl-form from the meso isomer: Collet, Synthesis 1973, 664.

Chemical structure

Derivative

dl-Form.

Properties

Crystals from ether + petr ether, mp 120°. Resolved into d- and l-forms by slow, repeated crystallizations from ether.

Derivative

d-Form.

Properties

[α]D20 +97.6° (chloroform).

Derivative

l-Form.

Properties

[α]D20 97.0° (chloroform).

Derivative

meso-Form.

Properties

Monoclinic leaflets from alcohol or water, mp 139°. Soly in water: 0.25% at 20°, 1.25% at 100°. Freely sol in hot alcohol, chloroform. Infrared absorption (chloroform): 2.82, 2.96μ. Dipole moment 2.67.