Iodine → Benzaldehyde, 4-hydroxy-3-iodo-5-methoxy-

HRID 358288

Reaktionsgleichung

Reaktionsgleichung von HRID 358288
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[Na+].[I-:13].OS(O)(=O)=O.II>[OH-].[Na+]>[I:13][C:10]1[C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=[C:3]([CH:11]=1)[CH:2]=[O:1]

Komponenten

6

Edukt 4

HCID 807IodineHCID 1118Sulfuric Acid2×HCID 1183VanillinHCID 5238Sodium Iodide

Produkt 1

HCID 79499Benzaldehyde, 4-hydroxy-3-iodo-5-methoxy-Ausbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Vanillin (28.4 g, 200 mmole (millimole)) was dissolved in 1N NaOH (200 ml) and warmed to 90° C. to avoid precipitation of sodium vanillate. A 2 molar aqueous solution of NaI3.NaI (105 ml, 210 mmole I2) plus 3.55 molar aqueous H2SO4 (5 ml) was added over 3 hours with stirring. The iodine color was discharged, and a pale tan stirrable precipitate formed. The solution was then cooled to room temperature, acidified to pH 2-3 with 20% aqueous H2SO4, and extracted with 10% methanol/90% chloroform. The organic phase was dried (MgSO4) and the solvent stripped to yield 53 g (99%) of 5-iodovanillin, more than 95% pure as analyzed by nuclear magnetic resonance spectroscopy (NMR).

Aufarbeitung

  1. customprecipitation of sodium vanillate
  2. customa pale tan stirrable precipitate formed
  3. temperatureThe solution was then cooled to room temperature
  4. extractionextracted with 10% methanol/90% chloroform
  5. dry with materialThe organic phase was dried (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-b93f7d28983548e283afb2b789cd9b20
Quelldatensatz
uspto-grants-1984_08
Patentnummer
US04465864

Verknüpfte Notizen

Wird geladen…