Vanillin → 4-(Difluoromethoxy)-3-methoxybenzaldehyde

HRID 727381Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 727381
Cl[CH:2]([F:4])[F:3].[O:5]=[CH:6][C:7]1[CH:15]=[CH:14][C:12]([OH:13])=[C:9]([O:10][CH3:11])[CH:8]=1.[OH-].[Na+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O1CCOCC1>[F:3][CH:2]([F:4])[O:13][C:12]1[CH:14]=[CH:15][C:7]([CH:6]=[O:5])=[CH:8][C:9]=1[O:10][CH3:11]

Komponenten

6

Edukt 3

HCID 1183VanillinHCID 6372ChlorodifluoromethaneHCID 14798Sodium Hydroxide

Produkt 1

HCID 31612494-(Difluoromethoxy)-3-methoxybenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5963Benzyltrimethylammonium chlorideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Chlorodifluoromethane is introduced into a mixture of 200 g of vanillin, 6.7 g of benzyltrimethylammonium chloride, 314 g of 50% strength sodium hydroxide solution and 2 liters of dioxane with vigorous stirring for about 2 h. The mixture is then partitioned between ice water and ethyl acetate, the organic phase is separated off, the aqueous phase is extracted twice by stirring with ethyl acetate, and the combined organic phases are dried over magnesium sulphate and concentrated in vacuo. To remove unreacted vanillin, the oil is chromatographed on neutral silica gel using toluene. After evaporating the eluate, 249 g of 4-difluoromethoxy-3-methoxybenzaldehyde are obtained as an oil.

Aufarbeitung

  1. customThe mixture is then partitioned between ice water and ethyl acetate
  2. customthe organic phase is separated off
  3. extractionthe aqueous phase is extracted twice
  4. stirringby stirring with ethyl acetate
  5. dry with materialthe combined organic phases are dried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customTo remove unreacted vanillin
  8. customthe oil is chromatographed on neutral silica gel
  9. customAfter evaporating the eluate, 249 g of 4-difluoromethoxy-3-methoxybenzaldehyde
  10. customare obtained as an oil

Quellen und Nachweise

ORD-Eintrag
ord-213cd97d73504a0ab088129ab9fe97dd
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05712298

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