Preparation of mandelic acid (2-hydroxy-2-phenylacetic

acid)

Preparation of mandelic acid (2-hydroxy-2-phenylacetic acid)

(A) 15 g of freshly distilled benzaldehyde are mixed with 50 ml of a saturated solution of sodium bisulfite. During the
reaction a semi-solid mass of the bisulfite compound sodium hydroxy(phenyl)methanesulfonate forms which after
standing for half an hour is filtered and washed with a little water and alcohol. The reaction mixture is then ground
into a thick paste with water, and a solution of 12 g of pure potassium cyanide or 8 g of sodium cyanide added. After
a short time the mandelonitrile separates as a reddish oil, to which a little ether is added and ethereal solution
of mandelonitrile is separated with separatory funnel. The ether is allowed to evaporate and (B)
mandelonitrile is hydrolyzed by continuing to heat on the water-bath with the addition of four to five times its
volume of conc, hydrochloric acid until crystals appear on the surface. Water is added and the hot liquid decanted
and filtered from any oil. On cooling, the crystals are filtered, washed with a little cold water, and dried. A further
quantity of mandelic acid can be extracted from the filtrate with ether. Yield of mandelic acid is 10-15g as
colorless needles with melting point 118-119 C.