반응 #64039

반응 방정식

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

수율 43.6%

용매

acetic acid

반응 조건

후처리

1. 1
   workup.WAITat room temperature over a period of 2 hours followed
2. 2
   온도by heating at 50° C. for 10 minutes
3. 3
   온도The resultant cooled solution
4. 4
   추출extracted with diethyl ether
5. 5
   세척The organic phase was washed three times with saturated sodium bicarbonate solution
6. 6
   건조twice with water, then dried over anhydrous sodium sulfate
7. 7
   기타The solvent was removed by evaporation under reduced pressure
8. 8
   기타a rotary evaporator
9. 9
   기타the resultant yellow solid recrystallized from ethanol

실험 절차

(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.

출처