반응 #60563

반응 방정식

methyl iodide

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

sodium hydride

→

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

수율 47.4%

용매

dimethylformamide

반응 조건

후처리

1. 1
   온도is heated for 1 hour to 50° C
2. 2
   온도heated for 4 hours to a bath temperature of 80° C
3. 3
   농축After concentration
4. 4
   기타by evaporation, it
5. 5
   추출extracted three times with 25 ml each of ethyl acetate
6. 6
   세척The ethyl acetate phase is washed with water
7. 7
   기타dried
8. 8
   여과filtered
9. 9
   농축concentrated by evaporation
10. 10
    기타The residue is chromatographed on 5 g of Isolute SI

실험 절차

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.

출처