Water → 3-Iodo-5-methoxy-4-propoxybenzaldehyde

HRID 1647754

Reaktionsgleichung

Reaktionsgleichung von HRID 1647754
[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(=O)([O-])[O-].[K+].[K+].[CH2:19](I)[CH2:20][CH3:21].O>CN(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][CH2:20][CH3:21])[CH:7]=[O:8]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 79499Benzaldehyde, 4-hydroxy-3-iodo-5-methoxy-

Produkt 1

HCID 47701013-Iodo-5-methoxy-4-propoxybenzaldehydeAusbeute 933,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Iodovanillin (25 g, 0.009 mol) in DMF (100 mL) was treated with potassium carbonate (32 g, 0.23 mol) and n-propyl iodide (52 g, 0.3 mol, 31 mL) and heated for 16 hours. The solution was allowed to cool to room temperature and then poured into water (500 mL) and extracted with ether (3×250 mL). The organic layers were combined and washed with water and saturated sodium chloride solution, and then dried over magnesium sulfate. The organic layer was evaporated by distillation under diminished pressure to an oil, and then purified by column chromatography (silica, 7:3 petroleum ether-ethyl acetate), to provide an amber colored solid (26.9 g, 93%).

Aufarbeitung

  1. temperatureheated for 16 hours
  2. extractionextracted with ether (3×250 mL)
  3. washwashed with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe organic layer was evaporated by distillation under diminished pressure to an oil
  6. custompurified by column chromatography (silica, 7:3 petroleum ether-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1d9eafbe08e34935bfbb2a60e6805491
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05434151

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