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

HRID 742501Notes

Reaction equation

HRID 742501 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:10](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH3:10][O:1][C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

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

Product 1

HCID 993521-Chloro-2-methoxy-4-methylbenzeneYield 93.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-hydroxy-4-chlorotoluene (25 g, 0.175 mol) in 400 ml of acetone was added 30.11 g (0.22 mol) of milled potassium carbonate and 31.22 g (0.22 mol) of methyl iodide, and the mixture was refluxed with stirring for 16 hours. The mixture was cooled, filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in ether, washed with water, and the organic layer was dried over sodium sulfate and concentrated in vacuo to afford 25.6 g of 3-methoxy-4-chlorotoluene as a solid.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in ether
  6. washwashed with water
  7. dry with materialthe organic layer was dried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-877c8ab11ee5499ca53e551ab68c390f
Source dataset
uspto-grants-1996_09
Patent number
US05554620

Reaction notes

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