4-Hydroxybenzaldehyde → 4-[(2,6-dichlorobenzyl)oxy]benzaldehyde

HRID 411737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 411737
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:12]=1[CH2:13]Br.[H-].[Na+]>CN(C)C=O>[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:12]=1[CH2:13][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 1264-HydroxybenzaldehydeHCID 24758Sodium hydrideHCID 301591-Bromomethyl-2,6-dichlorobenzene

Produkt 1

HCID 7354664-[(2,6-dichlorobenzyl)oxy]benzaldehydeAusbeute 107,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-hydroxybenzaldehyde (3.59 g, 24.39 mmol) and 2,6-dichlorobenzyl bromide (7.05 g, 29.39 mmol) in dimethylformamide (20 mL) at 0° C. was added 60% sodium hydride (1.176 g, 29.39 mmol). After stirring at ambient temperature for 16 h, the reaction was partitioned between ethyl acetate and water. The organic layer was washed with aqueous sodium chloride and dried (MgSO4). Purification by flash column chromatography (silica gel, hexane/ethyl acetate) yielded the title compound as an off-white solid (7.38 g, 89%).

Aufarbeitung

  1. customthe reaction was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with aqueous sodium chloride
  3. dry with materialdried (MgSO4)
  4. customPurification by flash column chromatography (silica gel, hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-5d7a1c1838f54022afafa11675904a05
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06559179B1

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