Methyl iodide → 1-Chloro-2-methoxy-4-methylbenzene

HRID 1869408Notes

Reaction equation

HRID 1869408 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].[C:10](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 120082-Chloro-5-methylphenol

Product 1

HCID 993521-Chloro-2-methoxy-4-methylbenzeneYield 103.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

50 g (350.65 mmol) of 2-chloro-5-methylphenol is dissolved in 450 ml of acetone and mixed with 96.5 g (701.3 mmol) of potassium carbonate under nitrogen. After 43.6 ml of methyl iodide (2 equivalents) is added, it is refluxed for three hours. After cooling, the reaction mixture is filtered, the filter residue is washed with acetone, and the filter is spun in until a dry state is reached (bath temperature 30° C.). Since the residue still contains potassium carbonate, it is taken up in a little diethyl ether and filtered again. After the solvent is spun off, 57 g (103.8%) of the desired compound is obtained, which is used as crude product in the next stage.

Workup

  1. temperatureit is refluxed for three hours
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered
  4. washthe filter residue is washed with acetone
  5. custom(bath temperature 30° C.)
  6. filtrationfiltered again

Sources & evidence

ORD record
ord-c08868ac64a74ee98c5473de91717926
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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