Water → 2-Hydroxy-4-(methoxymethoxy)benzaldehyde

HRID 1826644Notes

Reaction equation

HRID 1826644 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:17][O:18][CH2:19]Cl.O>C(#N)C>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:17][O:18][CH3:19])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 72132,4-DihydroxybenzaldehydeHCID 7864Chloromethyl Methyl EtherHCID 10796Cesium carbonate

Product 1

HCID 27550732-Hydroxy-4-(methoxymethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 2,4-dihydroxybenzaldehyde (0.83 g) and cesium carbonate (1.7 g) in acetonitrile (30 mL) was added chloromethyl methyl ether (0.55 mL), and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gal (eluent: hexane/ethyl acetate=4/1) to give 2-hydroxy-4-(methoxymethyloxy)benzaldehyde (0.84 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by column chromatography on silica gal (eluent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-a876f0c344a942eba96fe6f272ed419b
Source dataset
uspto-grants-2006_05
Patent number
US07053060B2

Reaction notes

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