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

HRID 510580Notes

Reaction equation

HRID 510580 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([OH:11])[C:3]=1[CH:4]=[O:5].[C:12](=O)([O-])[O-].[K+].[K+].IC.CCCCCC.CCOC(C)=O>CN(C=O)C.O>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([O:11][CH3:12])[C:3]=1[CH:4]=[O:5]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5283902,4-Dichloro-6-hydroxybenzaldehydeHCID 21226206Ethyl acetate hexane

Product 1

HCID 128028802,4-Dichloro-6-methoxybenzaldehydeYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2,4-dichloro-6-hydroxybenzaldehyde (1.85 g; 9.7 mmol) in 20 mL DMF at ambient temperature was added solid potassium carbonate (1.47 g; 10.6 mmol), and the resulting yellow mixture was stirred at ambient temperature. After 30 minutes, iodomethane (5.5 g; 38.7 mmol) was added, and the resulting mixture was stirred in an oil bath set to 50° C. After 10 minutes, the reaction was determined to be complete by thin layer chromatography (90/10 hexane/EtOAc). After a total of 30 minutes the mixture was cooled to ambient temperature and diluted with 200 mL water. After stirring for a few minutes, the precipitate that formed was collected by filtration, washed with water, and dried under vacuum to give 1.93 g of 2,4-dichloro-6-methoxybenzaldehyde as an off-white powder.

Workup

  1. stirringthe resulting mixture was stirred in an oil bath
  2. customset to 50° C
  3. waitAfter 10 minutes
  4. temperatureAfter a total of 30 minutes the mixture was cooled to ambient temperature
  5. stirringAfter stirring for a few minutes
  6. customthe precipitate that formed
  7. filtrationwas collected by filtration
  8. washwashed with water
  9. customdried under vacuum

Sources & evidence

ORD record
ord-44116caff36948248b3e39539183be09
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

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