Dimethylformamide → 4-(2-Hydroxyethoxy)-3-iodo-5-methoxybenzaldehyde

HRID 265628

Reaktionsgleichung

Reaktionsgleichung von HRID 265628
[I:1][C:2]1[C:3]([OH:12])=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:13](=[O:16])([O-])[O-].[K+].[K+].[CH3:19]N(C=O)C>>[CH3:11][O:10][C:4]1[CH:5]=[C:6]([CH:9]=[C:2]([I:1])[C:3]=1[O:12][CH2:19][CH2:13][OH:16])[CH:7]=[O:8]

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79499Benzaldehyde, 4-hydroxy-3-iodo-5-methoxy-

Produkt 1

HCID 17140644-(2-Hydroxyethoxy)-3-iodo-5-methoxybenzaldehydeAusbeute 57 %

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

5-Iodovanillin (25 g, 90 mmol) in DMF (100 mL) was added to potassium carbonate (18.6 g, 135 mmol). The mixture was heated at 40° C. for 16 hours. The reaction mixture was allowed to cool to room temperature and quenched with water (500 mL) and extracted with ethyl acetate. The organic layer was washed with water and saturated NaCl solution, and dried over MgSO4, filtered and evaporated in vacuo to an oil, and then purified by column chromatography (silica, 2:1 hexane/ethyl acetate), to provide the product (16.6 g, 57%). 1H NMR (CDCl3): 2.70 (t, 1H); 3.92 (t, 2H); 3.92 (s, 3H); 3.94 (s, 3H); 4.29 (t, 2H); 7.44 (s, 1H); 7.87 (s, 1H); 9.85 (s, 1H).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customquenched with water (500 mL)
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo to an oil
  8. custompurified by column chromatography (silica, 2:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-4826042750d2461395d7f2470d5c7dbb
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648486

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