反応 #64039

反応方程式

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

収率 43.6%

溶媒

acetic acid

反応条件

後処理

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
   抽出extracted with diethyl ether
5. 5
   洗浄The organic phase was washed three times with saturated sodium bicarbonate solution
6. 6
   乾燥twice with water, then dried over anhydrous sodium sulfate
7. 7
   その他The solvent was removed by evaporation under reduced pressure
8. 8
   その他a rotary evaporator
9. 9
   その他the resultant yellow solid recrystallized from ethanol

実験手順

(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.

出典