Reaktion #347267

Reaktionsgleichung

potassium tert.-butoxide

2-hydroxy-acetophenone

HCl

potassium tert.-butoxide

3-methoxy-2-nitrobenzoyl chloride

→

1-(2-hydroxyphenyl)-3-(3-methoxy-2-nitrophenyl)propane-1,3-dione

Ausbeute 94.1%

Lösungsmittel

THF

THF

CH2Cl2

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe temperature below 5° C
2. 2
   TemperaturThe resulting yellow paste is warmed to 25° C.
3. 3
   TemperaturThe mixture is cooled to 0° C.
4. 4
   Sonstigethe temperature below 5° C
5. 5
   TemperaturThe mixture is warmed to 25° C.
6. 6
   workup.STIRRINGstirred for 1 hour
7. 7
   TemperaturThe mixture is cooled to 5° C.
8. 8
   Sonstigeforming a dark brown paste
9. 9
   Temperaturthe mixture is heated
10. 10
    Temperaturat reflux for 3 hours
11. 11
    TemperaturThe mixture is cooled to 25° C.
12. 12
    EinengenThe mixture is concentrated under reduced pressure
13. 13
    Sonstigeto leave a brown solid
14. 14
    WaschenH2O (50 mL), washed with saturated NaHCO3 solution (200 mL), saturated brine (200 mL), and H2O (200 mL)
15. 15
    TrocknenThe organic layer is dried (Na2SO4)
16. 16
    Einengenconcentrated under reduced pressure

Vorschrift

To a 300-mL, three-neck, round-bottom flask with a mechanical stirrer is added potassium tert.-butoxide (2.5 g, 22 mmol). The flask is cooled to 0° C. and dry THF (10 mL) is added. To this solution, 2-hydroxy-acetophenone (3.5 mL, 18.6 mmol) in THF (10 mL) is added slowly over 30 minutes keeping the temperature below 5° C. The resulting yellow paste is warmed to 25° C. and stirred for 35 minutes. The mixture is cooled to 0° C. and 3-methoxy-2-nitrobenzoyl chloride (4.3 g, 20 mmol) in THF (15 mL) is added slowly over 15 minutes, keeping the temperature below 5° C. The mixture is warmed to 25° C. and stirred for 1 hour. The mixture is cooled to 5° C. and solid potassium tert.-butoxide (2.5 g, 22 mmol) is added forming a dark brown paste. THF (30 mL) is added and the mixture is heated at reflux for 3 hours. The mixture is cooled to 25° C. and 3N HCl is added until the pH falls to 2. The mixture is concentrated under reduced pressure to leave a brown solid. The brown solid is dissolved in CH2Cl2 (200 mL) and H2O (50 mL), washed with saturated NaHCO3 solution (200 mL), saturated brine (200 mL), and H2O (200 mL). The organic layer is dried (Na2SO4) and concentrated under reduced pressure to yield 1-(2-hydroxyphenyl)-3-(3-methoxy-2-nitrophenyl)propane-1,3-dione (5.52 g, 79%) as a tautomeric mixture.

Quelle