Methyl iodide → 3-Chloro-4-methoxybenzaldehyde

HRID 1370122Notes

Reaction equation

HRID 1370122 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[C:11](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 170223-Chloro-4-hydroxybenzaldehyde

Product 1

HCID 786193-Chloro-4-methoxybenzaldehydeYield 93.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-chloro-4-hydroxybenzaldehyde (153 g) in dimethylformamide (500 ml) was added potassium carbonate (203 g) under ice-cooling, followed by iodomethane (91.3 ml). After stirring at ambient temperature for 2 hours, the mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layer were washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The oily residue was triturated with n-hexane to obtain 3-chloro-4-methoxybenzaldehyde (156 g) as a white powder.

Workup

  1. temperaturecooling
  2. customthe mixture was partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe oily residue was triturated with n-hexane

Sources & evidence

ORD record
ord-35eb4cce4d9a41729d3f25b0a0cc9609
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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