Reacción #2267071

Ecuación de reacción

HNO3

4-methoxyphenylacetone

acetic anhydride

HNO3

→

10

Rendimiento 59.0%

4-Methoxy-3-nitrophenylacetone

Rendimiento 59.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe ice-bath was removed
2. 2
   OtroThe reaction was quenched
3. 3
   workup.ADDITIONby adding ice water
4. 4
   ExtracciónThe resulting solution was extracted with ethyl acetate three times
5. 5
   SecadoThe organic phase was dried over Na2SO4
6. 6
   OtroRemoval of the solvent under reduced pressure
7. 7
   Otroafforded crude product
8. 8
   OtroPurification of the crude product

Procedimiento

To a solution of 4-methoxyphenylacetone 9 (6.56 g, 4 mmol) in acetic anhydride (16 mmol) was added 90% HNO3 dropwise at −5° C. After adding HNO3, the ice-bath was removed and allowed to warm up to room temperature. The reaction was quenched by adding ice water. The resulting solution was extracted with ethyl acetate three times. The organic phase was dried over Na2SO4. Removal of the solvent under reduced pressure afforded crude product. Purification of the crude product by using silica gel column gave 10 (4.9 g, 59%). 1HNMR(CDCl3): 7.70 (d, J=2.1 Hz, 1H), 7.37 (dd, J=2.2 Hz, 8.5 Hz, 1H), 7.08 (d, J=8.5 Hz, 1H), 3.95 (s, 3H), 3.74 (s, 2H), 2.21 (s, 3H).

Fuente