Benzaldehyde → HCID 178472685, compound

Participants

Reaction Conditions

Reaction Steps

Glycine ethyl ester hydrochloride (69.1 g, 495 mmol) and toluene (215 g) were mixed, and N-methylpyrrolidone (32.5 g) was poured into the mixture at room temperature. Benzaldehyde (50.0 g, 471 mmol) was added dropwise to the obtained mixture, and then trimethyl orthoformate (52.5 g, 495 mmol) was added dropwise. After completion of the dropwise addition, the temperature of the obtained mixture was adjusted to 7° C. and a mixed solution of triethylamine (52.4 g, 518 mmol) and toluene (26.5 g) was added dropwise over 3 hours. After completion of the dropwise addition, the mixture was stirred at a temperature in a range from 7° C. to room temperature for 6 hours. After completion of the reaction, the reaction mixture was cooled to 5° C. and water (140 mL) was added dropwise thereto. Thereafter, stirring was stopped to perform liquid separation and then the obtained organic layer was washed with 20% brine (95 g). The obtained organic layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure to obtain a toluene solution (104.5 g) of (E)-N-phenylmethyleneglycine ethyl ester (86.9 g of pure (E)-N-phenylmethyleneglycine ethyl ester). Yield: 96%.

Provenance & Evidence