Reaktion #805991

Reaktionsgleichung

HNO3

HNO3

4-oxo-4-(p-tolyl)butanoic acid

4-Oxo-4-(p-tolyl)butanoic acid

→

4-(4-methyl-3-nitrophenyl)-4-oxobutanoic acid

Ausbeute 69.0%

4-(4-Methyl-3-nitrophenyl)-4-oxobutanoic acid

Ausbeute 69.0%

Lösungsmittel

H2SO4

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturmaintaining an internal temperature of less than 15° C
2. 2
   Temperaturmaintaining an internal temperature of less than 5° C
3. 3
   TemperaturAfter cooling to about −8° C.
4. 4
   Temperaturmaintaining the temperature below about 0° C
5. 5
   workup.ADDITIONAfter completion of addition the mixture
6. 6
   Temperaturto warm to about 15-17° C
7. 7
   workup.ADDITIONThe solution was poured
8. 8
   Sonstigeonto crushed ice
9. 9
   Filtrationthe solid was collected by filtration
10. 10
    Waschenwashing with water (3×10 L)
11. 11
    Sonstigedried

Vorschrift

HNO3 (65%) (2300 mL) was cooled to about 0° C. Fuming HNO3 (5700 mL) was carefully added maintaining an internal temperature of less than 15° C. The solution was cooled to about −5° C. and H2SO4 (800 mL) was added maintaining an internal temperature of less than 5° C. After cooling to about −8° C., 4-oxo-4-(p-tolyl)butanoic acid (72) (4000 g, 20.8 mol) was added portionwise maintaining the temperature below about 0° C. After completion of addition the mixture was allowed to warm to about 15-17° C. The solution was poured onto crushed ice with stirring. After about 2 h at rt, the solid was collected by filtration washing with water (3×10 L) and then dried to afford 4-(4-methyl-3-nitrophenyl)-4-oxobutanoic acid (73) (3400 g, 69% yield). 1H NMR (300 MHz, DMSO): δ 8.46 (s, 1H), 8.20 (d, J=8.4 Hz, 1H), 7.64 (d, J=8.0 Hz, 1H), 3.25 (m, 2H), 2.62 (m, 2H), 2.60 (s, 3H).

Quelle