反応 #2267071

反応方程式

HNO3

4-methoxyphenylacetone

acetic anhydride

HNO3

→

10

収率 59.0%

4-Methoxy-3-nitrophenylacetone

収率 59.0%

反応条件

後処理

1. 1
   その他the ice-bath was removed
2. 2
   その他The reaction was quenched
3. 3
   workup.ADDITIONby adding ice water
4. 4
   抽出The resulting solution was extracted with ethyl acetate three times
5. 5
   乾燥The organic phase was dried over Na2SO4
6. 6
   その他Removal of the solvent under reduced pressure
7. 7
   その他afforded crude product
8. 8
   その他Purification of the crude product

実験手順

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).

出典