Реакция #64039

Уравнение реакции

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

Выход 43.6%

Растворители

acetic acid

Условия реакции

Обработка

1. 1
   workup.WAITat room temperature over a period of 2 hours followed
2. 2
   Температураby heating at 50° C. for 10 minutes
3. 3
   ТемператураThe resultant cooled solution
4. 4
   Экстракцияextracted with diethyl ether
5. 5
   ПромывкаThe organic phase was washed three times with saturated sodium bicarbonate solution
6. 6
   Сушкаtwice with water, then dried over anhydrous sodium sulfate
7. 7
   ДругоеThe solvent was removed by evaporation under reduced pressure
8. 8
   Другоеa rotary evaporator
9. 9
   Другоеthe resultant yellow solid recrystallized from ethanol

Методика

(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.

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