2'-Hydroxyacetophenone → 1-{2-[(4-Nitrophenyl)methoxy]phenyl}ethan-1-one

Temperature

50 °C

To a stirred solution of 2′-hydroxyacetophenone (5.000 g, 36.724 mmol) in acetonitrile (200 mL) was added potassium carbonate (7.613 g, 55.086 mmol). The mixture was stirred at 50° C. for 30 min. 4-Nitrobenzyl bromide (8.727 g, 40.396 mmol) was added to the mixture, and the stirring was continued at 50° C. for 12 hrs. Potassium carbonate (0.508 g, 3.672 mmol) and 4-nitrobenzyl bromide (0.793 g, 3.672 mmol) were added to the mixture and the resulting mixture was stirred at 50° C. for 12 hrs. After cooled to room temperature, the reaction mixture was concentrated under reduced pressure and diluted with ethyl acetate. The organic phase was washed with water, dried over Na2SO4, filtered, and concentrated. The resulting residue was washed with hexane to give 1-{2-[(4-nitrobenzyl)oxy]phenyl}ethanone as a white solid. (8.900 g, yield; 89%)

1. waitthe stirring was continued at 50° C. for 12 hrs
2. stirringthe resulting mixture was stirred at 50° C. for 12 hrs
3. temperatureAfter cooled to room temperature
4. concentrationthe reaction mixture was concentrated under reduced pressure
5. additiondiluted with ethyl acetate
6. washThe organic phase was washed with water
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. washThe resulting residue was washed with hexane

ORD record

ord-295068d3d0224231950ed8c862006ab6

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06984649B1