Methyl iodide → 5-CHLORO-2-METHYLANISOLE

HRID 1178547Notes

Reaction equation

HRID 1178547 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1O.[C:10](=O)([O-])[O-:11].[K+].[K+].IC>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([O:11][CH3:10])[CH:3]=1

Participants

5

Reactant 3

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

Product 1

HCID 2928585-CHLORO-2-METHYLANISOLEYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Commercially available 2-chloro-5-methylphenol (19.8 g, 70 mmol) was dissolved in 450 ml acetone. Potassium carbonate (28.9 g, 209 mmol) was added, followed by iodomethane (29.7 g, 209 mmol), and the mixture was refluxed overnight with vigorous stirring. The mixture was then filtered and concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with water, dried with sodium sulfate, and concentrated giving 8.5 g 4-Chloro-2-methoxy-1-methyl-benzene (100%). 1H NMR (300 MHz, CDCl3) •2.28 (s, CH3, 3H), 3.92 (s, —OCH3, 3H), 6.91 (d, Ar, 1H, J=2.0 Hz), 6.95 (dd, Ar, 1H, J=8.0, 2.0 Hz), 7.14 (m, Ar, 1H).

Workup

  1. temperaturethe mixture was refluxed overnight with vigorous stirring
  2. filtrationThe mixture was then filtered
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9ae211b2277c47a882eda73f4cf34dd4
Source dataset
uspto-grants-2007_10
Patent number
US07276526B2

Reaction notes

Loading…