Water → HCID 66927727, Verbindung

HRID 131081

Reaktionsgleichung

Reaktionsgleichung von HRID 131081
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 66927727HCID 66927727, VerbindungAusbeute 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, 2 H), 3.26 (s, 3 H); 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-5e97ae47f478442a93f38cf080cab1a8
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384815B2

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