Ethyl chloroacetate → HCID 19363318, compound

Temperature

0 °C

1-(2-Methoxy-5-methylphenyl)heptan-1-one (81.6 g, 0.348 mol), ethyl chloroacetate (64 g, 0.522 mol) and benzene (100 ml) were mixed, and this solution was cooled to 0° C. Potassium t-butoxide (58.6 g, 0.522 mol) was added, and the mixture was stirred at room temperature for 0.5 hour. This solution was cooled again to 0° C. Then ethyl chloroacetate (32 g, 0.261 mol) and potassium t-butoxide (29.3 g, 0.261 mol) were added, and the mixture was stirred at room temperature for 0.5 hour. The reaction mixture was poured onto ice (200 g) to stop the reaction and the aqueous layer was extracted 3 times with toluene (120 ml). The organic layer was washed successively with water, an aqueous acetic acid solution (water/acetic acid=50/1) and water (100 ml each), and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. To the obtained residue were added ethanol (90 ml) and sodium ethoxide previously prepared from sodium (13.1 g, 0.567 mol) and ethanol (260 ml), and the mixture was stirred at room temperature for 1.5 hours. Water (17 ml) was added to the reaction mixture, and the mixture was stirred for 0.5 hour. Ethanol was evaporated under reduced pressure. To this residue, water (350 ml) and conc. hydrochloric acid (63 ml) were added, and the mixture was refluxed under heating for 1.5 hours. The aqueous layer was extracted 3 times with ether (200 ml). The organic layers were combined, washed successively with water, a saturated aqueous sodium hydrogencarbonate solution and saturated brine (100 ml each), and dried over anhydrous magnesium sulfate. The drying agent was filtered off, the filtrate was concentrated under reduced pressure, and the obtained residue was distilled under reduced pressure (450 pa, 155-160° C.) to give 2-(2-methoxy-5-methylphenyl)octanal (64.5 g, 74.6%/) as a colorless oil.

1. temperatureThis solution was cooled again to 0° C
2. stirringthe mixture was stirred at room temperature for 0.5 hour
3. additionThe reaction mixture was poured onto ice (200 g)
4. customthe reaction
5. extractionthe aqueous layer was extracted 3 times with toluene (120 ml)
6. washThe organic layer was washed successively with water
7. dry with materialan aqueous acetic acid solution (water/acetic acid=50/1) and water (100 ml each), and dried over anhydrous magnesium sulfate
8. filtrationThe drying agent was filtered off
9. concentrationthe filtrate was concentrated under reduced pressure
10. additionTo the obtained residue were added ethanol (90 ml) and sodium ethoxide
11. stirringthe mixture was stirred at room temperature for 1.5 hours
12. stirringthe mixture was stirred for 0.5 hour
13. customEthanol was evaporated under reduced pressure
14. additionTo this residue, water (350 ml) and conc. hydrochloric acid (63 ml) were added
15. temperaturethe mixture was refluxed
16. temperatureunder heating for 1.5 hours
17. extractionThe aqueous layer was extracted 3 times with ether (200 ml)
18. washwashed successively with water
19. dry with materiala saturated aqueous sodium hydrogencarbonate solution and saturated brine (100 ml each), and dried over anhydrous magnesium sulfate
20. filtrationThe drying agent was filtered off
21. concentrationthe filtrate was concentrated under reduced pressure
22. distillationthe obtained residue was distilled under reduced pressure (450 pa, 155-160° C.)

ORD record

ord-650aec4a5bbf4848b5ed1d21a9c7bd56

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06017919