873. Atrolactic Acid

Nomenclature

CAS number: 515-30-0
α-Hydroxy-α-methylbenzeneacetic acid; α-methylmandelic acid; 2-phenyllactic acid; α-hydroxy-α-phenylpropionic acid; 2-hydroxy-2-phenylpropionic acid; 2-phenyl-2-hydroxypropionic acid.
C9H10O3; mol wt 166.17.
C 65.05%, H 6.07%, O 28.88%.

Description and references

Prepd from acetophenone cyanohydrin: McKenzie, Clough, J. Chem. Soc. 101, 393 (1912); Freudenberg et al., Ann. 501, 213 (1932); Eliel, Freeman, Org. Synth. coll. vol. IV, 58 (1963).

Chemical structure

Derivative

dl-Form, hemihydrate.

Properties

Orthorhombic crystals from water, mp 88-90° (softening at 75°). Anhydr, mp 94.5° (obtained by drying the hemihydrate at 55° and 0.5 mm Hg). pKa (25°): 3.467. Soly of the anhydr acid in one liter of water at 18° = 17.04 g, at 25° = 21.17 g, at 30° = 25.65 g. Much more sol in boiling water. Slightly sol in petr ether.