Acetyl chloride → HCID 21872537, compound

Temperature

75 °C

In 150 g of THF was dissolved 14.9 g of triethanolamine. To the resulting solution was added 40.4 g of triethylamine. The resulting mixture was cooled over ice bath and 15.7 g of acetyl chloride was added dropwise at a temperature not exceeding 30° C. The reaction mixture was heated over an oil bath to 75° C. and heating was conducted for 2 hours under reflux. Then, 20.5 g of acetoxyacetyl chloride was added and the resulting mixture was heated under reflux for further 2 hours. After the reaction mixture was allowed to be cooled down, 100 g of water was added to terminate the reaction. The organic layer thus separated was added with 200 g of dichloromethane, and then washed with 100 g of water. The organic layer was concentrated under reduced pressure, followed by distillation under reduced pressure, whereby 18.3 g of N,N-bis(2-acetoxyethyl)-2-(acetoxyacetoxy)ethylamine was obtained as the title compound (boiling point: 153 to 155° C./24 Pa, yield: 55%).

1. temperatureThe resulting mixture was cooled over ice bath
2. customexceeding 30° C
3. temperatureheating
4. temperatureunder reflux
5. temperaturethe resulting mixture was heated
6. temperatureunder reflux for further 2 hours
7. temperatureto be cooled down
8. customto terminate
9. customthe reaction
10. customThe organic layer thus separated
11. additionwas added with 200 g of dichloromethane
12. washwashed with 100 g of water
13. concentrationThe organic layer was concentrated under reduced pressure
14. distillationfollowed by distillation under reduced pressure

ORD record

ord-9060a43fa3d942e6bdf47dbd83aaaa88

Source dataset

uspto-grants-2005_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06916593B2