Vanillin → 4-Formyl-2-methoxyphenyl trifluoromethanesulfonate

HRID 1186976Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1186976
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[F:18][C:19]([F:34])([F:33])[S:20](OC1C=CC([N+]([O-])=O)=CC=1)(=[O:22])=[O:21].CCOC(C)=O>CN(C=O)C>[F:18][C:19]([F:34])([F:33])[S:20]([O:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=1[O:6][CH3:7])(=[O:22])=[O:21]

Komponenten

6

Edukt 4

HCID 1183VanillinHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 5498704-Nitrophenyl trifluoromethanesulfonate

Produkt 1

HCID 108029624-Formyl-2-methoxyphenyl trifluoromethanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of vanillin (20.0 g, 131 mmol) in DMF (200 mL) at room temperature was added potassium carbonate (36 g, 263 mmol) and 4-nitrophenyl trifluoromethanesulfonate (54.0 g, 197 mmol) and the reaction mixture was stirred for 8 h. EtOAc (600 mL) was added to the reaction mixture and the organic layer was washed three times with water, dried, filtered, and concentrated. The crude compound was then purified by flash chromatography (ethylacetate/hexanes 1:9→3:7) to provide 4-formyl-2-methoxyphenyl trifluoromethanesulfonate.

Aufarbeitung

  1. washthe organic layer was washed three times with water
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude compound was then purified by flash chromatography (ethylacetate/hexanes 1:9→3:7)

Quellen und Nachweise

ORD-Eintrag
ord-99675710826f444084d85dfa532145c9
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673920B2

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