反応 #640537

反応方程式

hexane

2-iodo-nitrotoluene

potassium carbonate

diethyl ether

→

4-nitro-2-methylbenzoic acid

収率 31.2%

溶媒

ethyl acetate

water

N,N-dimethylformamide

water

反応条件

後処理

1. 1
   温度heated
2. 2
   温度The reaction was cooled
3. 3
   その他the organic layer separated
4. 4
   抽出extracted with ethyl acetate
5. 5
   洗浄washed with water, brine
6. 6
   乾燥dried over magnesium sulfate
7. 7
   ろ過filtered
8. 8
   濃縮concentrated
9. 9
   その他to yield 0.5 g of crude material
10. 10
    濃縮The filtrate was concentrated
11. 11
    その他recrystallized fom diethyl ether/hexane

実験手順

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).

出典