Benzaldehyde → HCID 178472685, compound

Participants

Reaction Conditions

Reaction Steps

Glycine ethyl ester hydrochloride (13.8 g (98.9 mmol)) and 50 g of toluene were mixed, and 10 g of dimethyl sulfoxide was flown thereinto at room temperature. Benzaldehyde (10.0 g (94.2 mmol)) was flown into the obtained mixture. The obtained mixture was adjusted to 12° C., and 16.5 g of a 25% aqueous sodium hydroxide solution (sodium hydroxide 104 mmol) was added dropwise over 3 hours. After completion of the dropwise addition, the obtained mixture was stirred at a temperature in a range from 11° C. to 13° C. for 20 hours. After completion of the reaction, the reaction mixture was cooled to 5° C., and 11.4 mL of water was added dropwise thereto. Thereafter, stirring was stopped to perform liquid separation, and the obtained organic layer was washed with 19 g of 20% by weight brine. The obtained organic layer was dried over magnesium sulfate, then the solvent was distilled off under reduced pressure to obtain 43.6 g of a toluene solution of (E)-N-phenylmethyleneglycine ethyl ester (16.5 g of pure (E)-N-phenylmethyleneglycine ethyl ester). Yield: 92%

Provenance & Evidence