Methyl iodide → 1-Chloro-2-methoxy-3-methylbenzene

HRID 1042356Notes

Reaction equation

HRID 1042356 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].CI.[C:12]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH3:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 68982-Chloro-6-methylphenolHCID 11430Potassium Carbonate

Product 1

HCID 134345771-Chloro-2-methoxy-3-methylbenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

2-Chloro-6-methyl-phenol (12.00 g, 84.20 mmol) was mixed with MeI (10.50 mL, 0.17 mol) and K2CO3 (17.40 g, 0.13 mol) in acetone in acetone and the resulting reaction mixture was refluxed for 14 hours. The reaction mixture was cooled to room temperature, and then concentrated. The residue was diluted with Et2O. The resulting solution was washed with H2O (3×150 mL) and brine (1×200 mL), then dried over MgSO4 and concentrated. Purification by column chromatography using hex:EtOAc (4:1) as the eluant afforded the title compound.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 14 hours
  3. concentrationconcentrated
  4. additionThe residue was diluted with Et2O
  5. washThe resulting solution was washed with H2O (3×150 mL) and brine (1×200 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customPurification by column chromatography

Sources & evidence

ORD record
ord-7988336ac1e94ff799bc3e16e2a1a0da
Source dataset
uspto-grants-2013_10
Patent number
US08557853B2

Reaction notes

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