Water → Methyl 4-formyl-3-methoxybenzoate

HRID 550274

Reaktionsgleichung

Reaktionsgleichung von HRID 550274
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][CH3:14].C(=O)([O-])[OH:16].[Na+].O>CS(C)=O>[CH:2]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][CH3:14])=[O:16]

Komponenten

5

Edukt 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoate

Produkt 1

HCID 10631650Methyl 4-formyl-3-methoxybenzoateAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of methyl 4-(bromomethyl)-3-methoxybenzoate (3.00 g, 11.6 mmol) in dimethyl sulfoxide (16 ml) was added sodium hydrogen carbonate (1.00 g, 13.6 mmol), and the mixture was stirred at 50° C. for 3 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous MgSO4 and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (1:0-7:3, v/v) to give the title compound (870 mg, 39%) as a colorless oil.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous MgSO4
  3. customthe solvent was evaporated under reduced pressure
  4. washeluted with hexane-ethyl acetate (1:0-7:3

Quellen und Nachweise

ORD-Eintrag
ord-d1776e362c9848ec84a0a987a3118b76
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943770B2

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