反应 #64039

反应方程式

nitric acid

acetic anhydride

3-Hydroxy-5-mesityl-2-propionylcyclohex-2-en-1-one

acetic anhydride

→

3-hydroxy-5-(2,4,6-trimethyl-3-nitrophenyl)-2-propionylcyclohex-2-en- 1-one

收率 43.6%

溶剂

acetic acid

反应条件

后处理

1. 1
   workup.WAITat room temperature over a period of 2 hours followed
2. 2
   温度by heating at 50° C. for 10 minutes
3. 3
   温度The resultant cooled solution
4. 4
   萃取extracted with diethyl ether
5. 5
   洗涤The organic phase was washed three times with saturated sodium bicarbonate solution
6. 6
   干燥twice with water, then dried over anhydrous sodium sulfate
7. 7
   其他The solvent was removed by evaporation under reduced pressure
8. 8
   其他a rotary evaporator
9. 9
   其他the resultant yellow solid recrystallized from ethanol

实验过程

(b) 3-Hydroxy-5-mesityl-2-propionylcyclohex-2-en-1-one (1.3 g; 4.5 mmole) was added to acetic anhydride (3.0 g) at 5° C. A solution of fuming nitric acid (0.42 g) in a glacial acetic acid (0.27 g)/acetic anhydride (0.27 g) solution was added to the cooled, stirred mixture dropwise over a period of 5 minutes. The mixture was maintained at 5° C. over a period of 1 hour and then at room temperature over a period of 2 hours followed by heating at 50° C. for 10 minutes. The resultant cooled solution was then poured into ice water (100 ml) and extracted with diethyl ether. The organic phase was washed three times with saturated sodium bicarbonate solution and twice with water, then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure using a rotary evaporator and the resultant yellow solid recrystallized from ethanol to give 3-hydroxy-5-(2,4,6-trimethyl-3-nitrophenyl)-2-propionylcyclohex-2-en- 1-one (0.65 g; 43.6%) as a yellow solid mp 174° C.

来源