Methyl iodide → 1-Methoxymethyloxy-2,3,4,5-tetramethoxybenzene

HRID 248558Notes

Reaction equation

HRID 248558 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[C:7]([O:15][CH3:16])[C:6]=1[OH:17].[C:18](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[C:7]([O:15][CH3:16])[C:6]=1[O:17][CH3:18]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 200957092-Methoxymethyloxy-4,5,6-trimethoxyphenol

Product 1

HCID 134955321-Methoxymethyloxy-2,3,4,5-tetramethoxybenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

11.5 g of 2-methoxymethyloxy-4,5,6-trimethoxyphenol prepared in Referential Example 12 and 23.0 g of potassium carbonate were suspended in 100 ml of DMF. The suspension was heated at 45° C. while stirring, and 5.2 ml of iodomethane was dropwise added thereto. After the completion of the dropwise addition, the mixture was heated for 30 min, cooled and separated by filtration. 1 l of water was added to the mother liquor, and the mixture was extracted with ethyl acetate. The organic phase was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (eluent; n-hexane : ethyl acetate=85 : 15) to prepare 6.2 g of the product compound as a colorless oleaginous substance.

Workup

  1. additionAfter the completion of the dropwise addition
  2. temperaturethe mixture was heated for 30 min
  3. temperaturecooled
  4. customseparated by filtration
  5. addition1 l of water was added to the mother liquor
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic phase was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off
  10. customThe residue was purified by silica gel column chromatography (eluent; n-hexane : ethyl acetate=85 : 15)
  11. customto prepare 6.2 g of the product compound as a colorless oleaginous substance

Sources & evidence

ORD record
ord-e0a1f68cf8774c448a93bebdd1f00271
Source dataset
uspto-grants-1993_05
Patent number
US05210239

Reaction notes

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