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

HRID 862054Notes

Reaction equation

HRID 862054 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:11])[C:6](=[CH:9][CH:10]=1)[CH:7]=[O:8].C(N(C(C)C)C(C)C)C.[CH3:21][O:22][CH2:23]Cl.O>ClCCl>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([O:11][CH2:21][O:22][CH3:23])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 696002-Hydroxy-4-MethoxybenzaldehydeHCID 81531Diisopropylethylamine

Product 1

HCID 3974214-methoxy-2-(methoxymethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-methoxysalicylaldehyde (7.54 g) and N-ethyl diisopropylamine (17 ml) in dichloromethane (250 ml) was cooled to 0° C., to which was added dropwise chloromethyl methyl ether (6.0 ml). The mixture was then warmed up to room temperature, which was stirred overnight. To the reaction mixture was added water to quench the reaction, which was subjected to extraction with chloroform. The organic layer was dried (anhydrous magnesium sulfate), then the solvent was distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane) to give 4-methoxy-2-methoxymethoxy benzaldehyde (8.82 g) (Compound B-4), whose physico-chemical properties are shown in Table 5.

Workup

  1. customto quench
  2. customthe reaction, which
  3. extractionwas subjected to extraction with chloroform
  4. dry with materialThe organic layer was dried (anhydrous magnesium sulfate)
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane)

Sources & evidence

ORD record
ord-369ade320d604d4491f5cb553a4056ad
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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