Reaction #725869

Reaction equation

water

Potassium carbonate

4-nitrophenol

13

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

→

product

Yield 77.1%

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

Yield 77.1%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   TemperatureAfter cooling to room temperature
2. 2
   Extractionextracted three times with methylene chloride
3. 3
   WashThe combined organic layers were washed with water
4. 4
   Dryingbrine, dried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Otherthe solvent was removed by distillation at reduced pressure

Procedure

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.

Source