Water → 3,4-Bis(methoxymethoxy)benzaldehyde

HRID 982893Notes

Reaction equation

HRID 982893 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[C:11](=[O:14])([O-])[O-].[K+].[K+].[CH3:17][O:18][CH2:19]Cl.O.[CH3:22]N(C=O)C>>[CH3:17][O:18][CH2:19][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:22][O:14][CH3:11])[CH:5]=[O:6]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 117463143,4-Bis(methoxymethoxy)benzaldehydeYield 42%

Procedure

3,4-Dihydroxybenzaldehyde (10 g, 67 mmol) was dissolved in DMF (50 mL), and potassium carbonate (20 g, 134 mmol) was added thereto, followed by stirring at room temperature for 30 minutes. Chloromethyl methyl ether (0.96 mL, 13 mmol) was added thereto, and the mixture was further stirred at room temperature for 20 hours. The reaction solution was poured into water and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluted with chloroform) to obtain 3,4-bis(methoxymethoxy)benzaldehyde (6.4 g; yield: 42%).

Workup

  1. stirringthe mixture was further stirred at room temperature for 20 hours
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluted with chloroform)

Sources & evidence

ORD record
ord-6991ae8d6f964089a9af87ca6eea7068
Source dataset
uspto-grants-2005_03
Patent number
US06861530B2

Reaction notes

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