反应 #60563

反应方程式

methyl iodide

2-hydroxy-4-nitro-benzoic acid methyl ester

sodium hydride

→

2-methoxy-4-nitro-benzoic acid methyl ester

收率 47.4%

溶剂

dimethylformamide

反应条件

后处理

1. 1
   温度is heated for 1 hour to 50° C
2. 2
   温度heated for 4 hours to a bath temperature of 80° C
3. 3
   浓缩After concentration
4. 4
   其他by evaporation, it
5. 5
   萃取extracted three times with 25 ml each of ethyl acetate
6. 6
   洗涤The ethyl acetate phase is washed with water
7. 7
   其他dried
8. 8
   过滤filtered
9. 9
   浓缩concentrated by evaporation
10. 10
    其他The residue is chromatographed on 5 g of Isolute SI

实验过程

788 mg (4 mmol) of 2-hydroxy-4-nitro-benzoic acid methyl ester is mixed in 20 ml of absolute dimethylformamide with 177 mg of sodium hydride (60%; 4.4 mmol), and it is heated for 1 hour to 50° C. After cooling to room temperature, it is mixed with 625 mg (4.4 mmol) of methyl iodide and heated for 4 hours to a bath temperature of 80° C. After concentration by evaporation, it is taken up in 50 ml of water and extracted three times with 25 ml each of ethyl acetate. The ethyl acetate phase is washed with water, dried, filtered and concentrated by evaporation. The residue is chromatographed on 5 g of Isolute SI. (50 μm) with a gradient from cyclohexane to cyclohexane:ethyl acetate=80:20 as an eluant, and 400 mg (47% of theory) of 2-methoxy-4-nitro-benzoic acid methyl ester is obtained as an oil.

来源