Methyl iodide → 2,6-Dichloro-4-methoxybenzaldehyde

HRID 75240

Reaktionsgleichung

Reaktionsgleichung von HRID 75240
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5].[C:12](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH3:12])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5]

Komponenten

7

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5283822,6-Dichloro-4-hydroxybenzaldehyde

Produkt 1

HCID 147717592,6-Dichloro-4-methoxybenzaldehydeAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 2,6-dichloro-4-hydroxybenzaldehyde (225 mg, 1.18 mmol) in DMF (2.0 mL) was added potassium carbonate (0.81 g, 5.9 mmol) and methyl iodide (1.47 mL, 23.6 mmol). The resulting mixture was heated at 80° C. for 3 h. Reaction was diluted with water and ethyl acetate. The organic layer was separated and dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (20% ethyl acetate/hex) to give the desired product as a white solid (210 mg, 87%). LCMS for C8H7Cl2O2(M+H)+: m/z=205.

Aufarbeitung

  1. customReaction
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (20% ethyl acetate/hex)

Quellen und Nachweise

ORD-Eintrag
ord-3f7d0ea6b41442eeb9748a025c22cb0b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835423B2

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