Reacción #725869

Ecuación de reacción

water

Potassium carbonate

4-nitrophenol

13

2-[2-(2-methoxyethoxy)ethoxy]ethyl p-toluenesulfonate

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product

Rendimiento 77.1%

4-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}nitrobenzene

Rendimiento 77.1%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling to room temperature
2. 2
   Extracciónextracted three times with methylene chloride
3. 3
   LavadoThe combined organic layers were washed with water
4. 4
   Secadobrine, dried over magnesium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Otrothe solvent was removed by distillation at reduced pressure

Procedimiento

A portion of 13 (9.0 g, 28.3 mmol) was dissolved in 50 mL of dimethylformamide. Potassium carbonate (11.75 g, 85.0 mmol) and 4-nitrophenol (3.82 g, 27.5 mmol) were added. The solution was stirred at 80° C. for 16 hours. After cooling to room temperature, the solution was poured into water and extracted three times with methylene chloride. The combined organic layers were washed with water, then brine, dried over magnesium sulfate, filtered, and the solvent was removed by distillation at reduced pressure. Chromatography (silica, hexane:ethyl acetate, 1:2) was employed to isolate the product (5.71 g, 73% yield). IR (neat) 3109.2, 3078.2, 2878.5, 1726.3, 1588.1, 1511.2, 1337.1, 1106.7, 1050.3, 932.6, 845.5, 753.3, 656.1 cm−1. 1H NMR (CDCl3) δ 8.07 (d, J=9.3 Hz, 2H), 6.88 (d, J=9.3 Hz, 2H), 4.12 (app t, 2H), 3.79 (app t, 2H), 3.62 (m, 2H), 3.58 to 3.53 (m, 4H), 3.44 to 3.42 (m, 2H), 3.26 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 164.29, 141.93, 126.24, 114.99, 72.29, 71.29, 71.03, 70.98, 69.77, 68.60, 59.44.

Fuente