反应 #640537

反应方程式

hexane

2-iodo-nitrotoluene

potassium carbonate

diethyl ether

→

4-nitro-2-methylbenzoic acid

收率 31.2%

溶剂

ethyl acetate

water

N,N-dimethylformamide

water

反应条件

后处理

1. 1
   温度heated
2. 2
   温度The reaction was cooled
3. 3
   其他the organic layer separated
4. 4
   萃取extracted with ethyl acetate
5. 5
   洗涤washed with water, brine
6. 6
   干燥dried over magnesium sulfate
7. 7
   过滤filtered
8. 8
   浓缩concentrated
9. 9
   其他to yield 0.5 g of crude material
10. 10
    浓缩The filtrate was concentrated
11. 11
    其他recrystallized fom diethyl ether/hexane

实验过程

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).

来源