Reaktion #640537

Reaktionsgleichung

hexane

2-iodo-nitrotoluene

potassium carbonate

diethyl ether

→

4-nitro-2-methylbenzoic acid

Ausbeute 31.2%

Lösungsmittel

ethyl acetate

water

N,N-dimethylformamide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   TemperaturThe reaction was cooled
3. 3
   Sonstigethe organic layer separated
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   Waschenwashed with water, brine
6. 6
   Trocknendried over magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   Sonstigeto yield 0.5 g of crude material
10. 10
    EinengenThe filtrate was concentrated
11. 11
    Sonstigerecrystallized fom diethyl ether/hexane

Vorschrift

A mixture of 1.0 g (3.8 mmol) of 2-iodo-nitrotoluene, 2.1 g (15.2 mmol) potassium carbonate and 27 mg (0.038 mmol) of palladium(II) dichloride bis(triphenylphosphine) in a mixture of 5 mL of water and 10 mL of N,N-dimethylformamide. This was placed in a Fisher/Porter bottle under 15 psig of carbon monoxideand heated at 70° C. for 16 hours. The solution became homogeneous when heated. The reaction was cooled, diethyl ether and water was added, the organic layer separated and discarded. The aqueous layer was acidified with IN hydrohloric acid, extracted with ethyl acetate, washed with water, brine, dried over magnesium sulfate, filtered and concentrated to yield 0.5 g of crude material. This dissolved in ethyl acetate, hexane added and the resulting brown solid discarded. The filtrate was concentrated, and then recrystallized fom diethyl ether/hexane to afford 215 mg of 4-nitro-2-methylbenzoic acid, m/e=182 (M+H).

Quelle