Methyl iodide → 2-Chloro-4-methoxytoluene

HRID 1013786Notes

Reaction equation

HRID 1013786 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].IC.[C:12](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][CH3:12])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 148533-Chloro-4-methylphenol

Product 1

HCID 69517572-Chloro-4-methoxytolueneYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Heat a solution of 3-chloro-4-methylphenol (15 g, 0.11 mol), iodomethane (9.8 mL, 0.16 mol), and potassium carbonate (22 g, 0.16 mol) in DMF (200 mL) to 50° C. and stir for 2 hr. Cool the reaction to room temperature and quench with 1N aqueous HCl. Extract the aqueous with diethyl ether (Et2O). Wash the organic with brine, dry over MgSO4, and filter. Remove the solvent to afford 16.4 g (100%) of the desired product.

Workup

  1. temperatureCool
  2. customthe reaction to room temperature
  3. customquench with 1N aqueous HCl
  4. extractionExtract the aqueous with diethyl ether (Et2O)
  5. washWash the organic with brine
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. customRemove the solvent

Sources & evidence

ORD record
ord-d168a76031df44358b0c55dd138efc72
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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