Methyl iodide → 3-Chloro-2-methylanisole

HRID 1871059Notes

Reaction equation

HRID 1871059 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[CH3:9].[C:10](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:10])[C:3]=1[CH3:9]

Participants

5

Conditions

Temperature
80 °C

Procedure

To 100 ml DMF, was dissolved 3-chloro-o-cresol in an amount of 13.6 g (0.095 mole), and the resulting solution was then stirred for 2 hours at 80° C. following to the addition of potassium carbonate in an amount of 14.5 g (0.105 mole) and methyl iodide in an amount of 17.6 g (0.124 mole) into the solution at an ambient temperature. After cooling the mixture, insoluble materials therein were separated by filtration, and the mixture was then poured into water and extracted with ethyl ether. The organic layer obtained was washed with saturated saline solution and dried with anhydrous magnesium sulfate, and the solvent remained in the layer was distillated out to obtain 2-chloro-6-methoxytoluene in an amount of 14.6 g. The yield was 95.4%.

Workup

  1. temperatureAfter cooling the mixture, insoluble materials
  2. customtherein were separated by filtration
  3. additionthe mixture was then poured into water
  4. extractionextracted with ethyl ether
  5. customThe organic layer obtained
  6. washwas washed with saturated saline solution
  7. dry with materialdried with anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-ab2301936d2f492f828aa9eb5d5e0756
Source dataset
uspto-grants-2000_08
Patent number
US06100421

Reaction notes

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