Water → 4-{2-[2-(2-Methoxyethoxy)ethoxy]ethyl}nitrobenzene

HRID 638687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 638687
C1(C)C=CC(S(O[CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].[N+:28]([C:31]1[CH:36]=[CH:35][C:34](O)=[CH:33][CH:32]=1)([O-:30])=[O:29].O>CN(C)C=O>[CH3:20][O:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH2:12][CH2:11][C:34]1[CH:35]=[CH:36][C:31]([N+:28]([O-:30])=[O:29])=[CH:32][CH:33]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 99488982-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

Produkt 1

HCID 669277274-{2-[2-(2-Methoxyethoxy)ethoxy]ethyl}nitrobenzeneAusbeute 77,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionextracted three times with methylene chloride
  3. washThe combined organic layers were washed with water
  4. dry with materialbrine, dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed by distillation at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-51b1f0cc875c4b5e9466f12f6d3ee71f
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691359B2

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