Benzaldehyde → 1-Hydroxy-3-phenylpropan-2-one

Participants

Reaction Conditions

Reaction Steps

9.5 ml of 0.1 M citric acid and 40.5 ml of 0.1 M tri-sodium citrate were diluted to 100 ml to give a pH 6 citrate buffer solution. (Ref.: Buffers for pH and Metal Ion Control, D. D. Perrin and B. Dempsey, Publ. John Wiley and Sons, pg 103). Petroleum spirit (40 ml), ethanol (0.5 ml), the pH 6 citrate buffer (5 ml) and sodium pyruvate (2.5 g, 23 mmol) were stirred at room temperature for 1 h. Benzaldehyde (127 mg, 1.2 mmol) and baker's yeast (5 g) were then added and the reaction stirred at 5° C. for 24 h. The mixture was then filtered and yeast washed with diethyl ether. After removal of the solvent in vacuo the product was purified by flash distillation (200° C./1 mm) to give phenylacetylcarbinol (44 mg, 24%). The GC of the product showed pure PAC (11.88 min.). Chiral GC showed a ratio of 97.5:2.5, 95% ee.

Provenance & Evidence