Water → 2-(Methoxymethoxy)benzaldehyde

HRID 1821657Notes

Reaction equation

HRID 1821657 reaction equation
[H-].[Na+].Cl[CH2:4][O:5][CH3:6].O.[CH:8](=[O:16])[C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[OH:11]>CN(C)C=O>[CH3:6][O:5][CH2:4][O:11][C:10]1[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=1[CH:8]=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6998SalicylaldehydeHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydride

Product 1

HCID 108774852-(Methoxymethoxy)benzaldehydeYield 95.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide (20 mL) was dissolved 5.01 g (41.1 mmol) of commercially available salicylaldehyde, 1.80 g (45.0 mmol) of 60% sodium hydride was added to the solution in an ice bath, and after stirring the mixture in an ice bath for 10 minutes, 3.43 mL (45.2 mmol) of chloro(methoxy)methane was gradually added dropwise to the mixture and the resulting mixture was stirred in an ice bath for 1 hour. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was successively washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed, and the obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane-ethyl acetate, gradient) to obtain 6.54 g (39.4 mmol, Yield: 95.9%) of 2-(methoxymethoxy)benzaldehyde.

Workup

  1. additionwas added to the solution in an ice bath
  2. stirringthe resulting mixture was stirred in an ice bath for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was successively washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed
  7. customthe obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane-ethyl acetate, gradient)

Sources & evidence

ORD record
ord-be64e627ba4644ef8598c05920474b05
Source dataset
uspto-grants-2009_10
Patent number
US07608563B2

Reaction notes

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