Reaktion #64039

Reaktionsgleichung

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

Ausbeute 43.6%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITat room temperature over a period of 2 hours followed
2. 2
   Temperaturby heating at 50° C. for 10 minutes
3. 3
   TemperaturThe resultant cooled solution
4. 4
   Extraktionextracted with diethyl ether
5. 5
   WaschenThe organic phase was washed three times with saturated sodium bicarbonate solution
6. 6
   Trocknentwice with water, then dried over anhydrous sodium sulfate
7. 7
   SonstigeThe solvent was removed by evaporation under reduced pressure
8. 8
   Sonstigea rotary evaporator
9. 9
   Sonstigethe resultant yellow solid recrystallized from ethanol

Vorschrift

(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.

Quelle