Methyl iodide → 1,2-Dichloro-3,4-dimethoxybenzene

HRID 1089165

Reaction equation

HRID 1089165 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[C:4]([OH:9])[C:3]=1O.[C:11](=[O:14])([O-])[O-].[K+].[K+].[CH3:17]I>CC(C)=O>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([O:9][CH3:17])=[C:3]([O:14][CH3:11])[C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 198773,4-Dichlorocatechol

Product 1

HCID 560611,2-Dichloro-3,4-dimethoxybenzeneYield 91.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 104 g of 3,4-dichloro-1,2benzenediol, 240 g of potassium carbonate and 354 g of methyl iodide in 2 litters of acetone is refluxed for 2 hours. The reaction mixture is filtered and washed with acetone. The filtrate and the washings are combined and evaporated to remove solvent. Water is added to the residue and the mixture is extracted with ethyl acetate. The extract is washed with water, dried and evaporated to remove solvent. The residue is distilled under reduced pressure to give 110.5 g of 1,2-dichloro-3,4-dimethoxybenzene.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washwashed with acetone
  3. customevaporated
  4. customto remove solvent
  5. additionWater is added to the residue
  6. extractionthe mixture is extracted with ethyl acetate
  7. washThe extract is washed with water
  8. customdried
  9. customevaporated
  10. customto remove solvent
  11. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-f72ad2b3f3e84e9dbe031e901cc2b23e
Source dataset
uspto-grants-1990_10
Patent number
US04965282

Linked notes

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