Reacción #60563

Ecuación de reacción

methyl iodide

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

sodium hydride

→

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

Rendimiento 47.4%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturais heated for 1 hour to 50° C
2. 2
   Temperaturaheated for 4 hours to a bath temperature of 80° C
3. 3
   ConcentraciónAfter concentration
4. 4
   Otroby evaporation, it
5. 5
   Extracciónextracted three times with 25 ml each of ethyl acetate
6. 6
   LavadoThe ethyl acetate phase is washed with water
7. 7
   Otrodried
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated by evaporation
10. 10
    OtroThe residue is chromatographed on 5 g of Isolute SI

Procedimiento

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.

Fuente