Vanillin → 3-Methoxy-4-(methoxymethoxy)benzaldehyde

HRID 1457597Notes

Reaction equation

HRID 1457597 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=[O:10])[CH:6]=[CH:5][C:4]=1[OH:11].C(N(C(C)C)CC)(C)C.[CH3:21][O:22][CH2:23]Cl>O1CCCC1>[CH:9]([C:7]1[CH:6]=[CH:5][C:4]([O:11][CH2:21][O:22][CH3:23])=[C:3]([O:2][CH3:1])[CH:8]=1)=[O:10]

Participants

5

Reactant 3

HCID 1183VanillinHCID 7864Chloromethyl Methyl EtherHCID 81531Diisopropylethylamine

Product 1

HCID 796613-Methoxy-4-(methoxymethoxy)benzaldehydeYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixed solution of 15.2 g of 2-methoxy-4-formylphenol, 26 ml of diisopropyl ethylamine, 9 ml of methoxymethyl chloride and 100 ml of tetrahydrofuran (THF) was stirred at room temperature for 3.5 hours. The solvent was removed under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate. The extract was washed and dried, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=4:1) to give 18.9 g of (4-formyl-2-methoxyphenoxy)methoxymethane (yield: 96%, melting point: 34°-37° C.).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed
  5. customdried
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-1d87a20c60254778b9115cf7a7d3dc25
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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