반응 #640537

반응 방정식

hexane

2-iodo-nitrotoluene

potassium carbonate

diethyl ether

→

4-nitro-2-methylbenzoic acid

수율 31.2%

용매

ethyl acetate

water

N,N-dimethylformamide

water

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도The reaction was cooled
3. 3
   기타the organic layer separated
4. 4
   추출extracted with ethyl acetate
5. 5
   세척washed with water, brine
6. 6
   건조dried over magnesium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated
9. 9
   기타to yield 0.5 g of crude material
10. 10
    농축The filtrate was concentrated
11. 11
    기타recrystallized fom diethyl ether/hexane

실험 절차

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).

출처