Ethylene Glycol → HCID 19026967, Verbindung

HRID 1032952

Reaktionsgleichung

Reaktionsgleichung von HRID 1032952
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH2:14](O)[CH2:15][OH:16].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:15]1[O:16][C:8]([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=2)([CH3:9])[O:10][CH2:14]1

Komponenten

5

Edukt 3

HCID 174Ethylene GlycolHCID 1387234-Hydroxy-3-NitroacetophenoneHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 19026967HCID 19026967, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A solution of 4'-hydroxy-3'-nitroacetophenone (known compound, 12.1 g, 67.0 mmol), benzene (100 ml), ethylene glycol (5.61 ml, 100 mmol) and p-toluenesulfonic acid hydrate (catalytic amount) was refluxed overnight removing the resulting water by azeotropic distillation with benzene. To the reaction mixture was added a saturated aqueous solution of sodium hydrogencarbonate, and the mixture was extracted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel to give the object compound (1) as an oil. Yield 14.6 g (97%).

Aufarbeitung

  1. customremoving the resulting water
  2. distillationby azeotropic distillation with benzene
  3. additionTo the reaction mixture was added a saturated aqueous solution of sodium hydrogencarbonate
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-6c321d6e3ba54553a3cc0d0e00c56065
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05308840

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