Citric Acid → N-(4-Methoxy-2-methylphenyl)-acetamide

4-Methoxy-2-methylaniline (26.06 g, 190 mmol) and triethylamine (43 ml, 309 mmol) were dissolved in dichloromethane, acetic anhydride (25 ml, 265 mmol) was added under ice-cooling, and the mixture was stirred at the same temperature for 80 min. To the reaction mixture was added 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with diluted hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained solid was filtered, washed with hexane, and dried under reduced pressure to give the title compound (30.78 g, yield 90%) as a pale-pink solid.

1. temperaturecooling
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with diluted hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationThe insoluble material was filtered off
6. concentrationthe solution was concentrated under reduced pressure
7. filtrationThe obtained solid was filtered
8. washwashed with hexane
9. customdried under reduced pressure

ORD record

ord-014846d8cbeb4bd8a0d896903e06c714

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513235B2