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

HRID 75240

Reaction equation

HRID 75240 reaction equation
[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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-3f7d0ea6b41442eeb9748a025c22cb0b
Source dataset
uspto-grants-2014_09
Patent number
US08835423B2

Linked notes

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