Methyl iodide → HCID 14520331, compound

HRID 1194365Notes

Reaction equation

HRID 1194365 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([CH2:10][O:11][CH3:12])[C:3]=1[OH:13].CI.[C:16](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([CH2:10][O:11][CH3:12])[C:3]=1[O:13][CH3:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14520330HCID 14520330, compound

Product 1

HCID 14520331HCID 14520331, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

24.1 g (0.098 mole) of 2-bromo-3-methoxy-6-methoxymethylphenol and 27.7 g of methyl iodide are dissolved in 200 ml of acetone in the presence of 14.82 g (0.107 mole) of potassium carbonate. This solution is heated at reflux temperature, with stirring, for 2.5 hours. It is then cooled, the mineral salts are filtered off and the filtrate is distilled to remove the acetone. The residue is taken up in water and extracted with dichloromethane. The organic phase is dried over anhydrous sodium sulfate and distilled under reduced pressure. 13.1 g of 1-bromo-2,6-dimethoxy-3-methoxymethylbenzene are obtained. Yield: 51% of theory; B.P.: 92°-115° C./0.005 mbar.

Workup

  1. temperatureThis solution is heated
  2. temperatureat reflux temperature
  3. temperatureIt is then cooled
  4. filtrationthe mineral salts are filtered off
  5. distillationthe filtrate is distilled
  6. customto remove the acetone
  7. extractionextracted with dichloromethane
  8. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  9. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-c2ab4378a0ca43ae87e53b8371134a97
Source dataset
uspto-grants-1989_03
Patent number
US04814343

Reaction notes

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