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

HRID 1934707Notes

Reaction equation

HRID 1934707 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>CN(C)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 102.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-5-methylphenol (5.00 g) and potassium carbonate (7.27 g) in anhydrous dimethylformamide (30 mL) was added methyl iodide (3.27 mL), and the mixture was stirred for 3 hours at ambient temperature. The mixture was partitioned between water and ethyl acetate. The separated organic layer was washed with water and brine and dried over magnesium sulfate. The resultant was evaporated in vacuo to give 4-chloro-3-methoxytoluene as a colorless oil (5.65 g).

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. washThe separated organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe resultant was evaporated in vacuo

Sources & evidence

ORD record
ord-36da7b30fde642e3ac35d22525144667
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

Loading…