Benzaldehyde → Methyl 3-hydroxy-3-phenylpropanoate

Participants

Reaction Conditions

Reaction Steps

At room temperature, a three-neck flask equipped with a reflux condenser, internal thermometer, dropping funnel and stirrer under nitrogen protective gas was initially charged with 7.6 g of zinc powder (115 mmol) in 45 ml of isopropyl acetate. After 1.83 ml of trimethylchlorosilane (14 mmol) had been added, the mixture was heated to 60° C. for 15 min, then allowed to cool to 55° C. and 16.3 g of undiluted methyl bromoacetate (107 mmol) were subsequently added dropwise within 5 min, and the temperature was maintained at 60° C. by external cooling. The mixture was then stirred at 50° C. for 15 min. After cooling to 30° C., 9.4 g of undiluted benzaldehyde (89 mmol) were added, and the temperature was maintained at 40° C. by external cooling. After stirring had been continued at 40° C. for 30 min, the mixture was cooled to 0° C., acidified with 20 ml of 20% hydrochloric acid to a pH of 1 and the mixture was stirred for 30 min, during which excess zinc dissolved. The organic phase was then removed. The organic phase was then stirred with 30 ml of concentrated ammonia solution at 0° C. for 10 min. After the phase separation, drying was effected over sodium sulfate and the solvent was distilled off under reduced pressure. Methyl 3-hydroxy-3-phenylpropionate was obtained in a yield of 14.3 g (89% of theory) and had a boiling point of 78° C. (0.08 mbar).

Provenance & Evidence