Benzaldehyde → HCID 178472685, compound

Temperature

5 °C

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%

1. customat room temperature
2. customwas adjusted to 12° C.
3. additionAfter completion of the dropwise addition
4. customAfter completion of the reaction
5. stirringThereafter, stirring
6. customliquid separation
7. washthe obtained organic layer was washed with 19 g of 20% by weight brine
8. dry with materialThe obtained organic layer was dried over magnesium sulfate
9. distillationthe solvent was distilled off under reduced pressure

ORD record

ord-e09b17ea1e0c46f1920f950702429826

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09259723B2