Water → 2-Benzyloxy-5-methoxy-benzaldehyde

HRID 554514

Reaktionsgleichung

Reaktionsgleichung von HRID 554514
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C)C=O>[CH2:18]([O:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 956952-Hydroxy-5-methoxybenzaldehyde

Produkt 1

HCID 8784742-Benzyloxy-5-methoxy-benzaldehydeAusbeute 100,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-hydroxy-5-methoxybenzaldehyde (3.0 g, 19.7 mmol) in N,N-dimethylformamide (50 mL), potassium carbonate (3.27 g, 23.6 mmol) was added and furthermore benzyl bromide (2.6 mL, 21.7 mmol) was added thereto. The reaction mixture was stirred at room temperature for 24 hours, and then water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:4)] to obtain the title compound (4.8 g, 100%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. distillationthe solvent was distilled under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:4)]

Quellen und Nachweise

ORD-Eintrag
ord-283e8ac0f2c54904a4cc7d3105acedfc
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048897B2

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