Dimethylformamide → 1-Methoxymethyloxy-3,4,5-trimethoxyphenol

HRID 248555

Reaction equation

HRID 248555 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:13])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[H-].[Na+].[CH3:16][O:17][CH2:18]Cl.CN(C=[O:24])C>>[CH3:16][O:17][CH2:18][O:13][C:5]1([OH:24])[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH2:4]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 695053,4,5-Trimethoxyphenol

Product 1

HCID 677585271-Methoxymethyloxy-3,4,5-trimethoxyphenol

Procedure

25 g of 3,4,5-trimethoxyphenol was dissolved in 100 ml of DMF, and 7.1 g of sodium hydride, (55% oil suspension) was added thereto and cooled by ice while stirring. Then, 12.4 ml of methoxymethyl chloride was added thereto with ice cooling, and the mixture was stirred at room temperature for 30 min. The reaction mixture was poured into ice water and 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 30.4 g of the product compound as a colorless oleaginous substance.

Workup

  1. temperaturecooled by ice
  2. stirringwith ice cooling, and the mixture was stirred at room temperature for 30 min
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by silica gel column chromatography (eluent; n-hexane : ethyl acetate=85 : 15)
  8. customto prepare 30.4 g of the product compound as a colorless oleaginous substance

Sources & evidence

ORD record
ord-b1ed54475b8b463aac09225138b2d266
Source dataset
uspto-grants-1993_05
Patent number
US05210239

Linked notes

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