Water → 4-(Methoxymethoxy)-3,5-dimethylbenzaldehyde

HRID 1648462Notes

Reaction equation

HRID 1648462 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:11])[C:9]=1[OH:10])[CH:5]=[O:6].[H-].[Na+].Cl[CH2:15][O:16][CH3:17].O>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:11])[C:9]=1[O:10][CH2:15][O:16][CH3:17])[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 752223,5-Dimethyl-4-hydroxybenzaldehyde

Product 1

HCID 199197474-(Methoxymethoxy)-3,5-dimethylbenzaldehydeYield 94.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 9.0 g of 3,5-dimethyl-4-hydroxybenzaldehyde in 20 ml of dimethylformamide was added dropwise and whilst ice-cooling to a suspension of 3.14 g of a 55% w/w dispersion of sodium hydride in 50 ml of dimethylformamide. The mixture was then stirred for 20 minutes, after which 5.8 g of methyl chloromethyl ether were added, whilst ice-cooling. The resulting mixture was then stirred at room temperature for one hour. At the end of this time, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was then washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure to give 11.0 g of the title compound.

Workup

  1. temperaturecooling
  2. stirringThe resulting mixture was then stirred at room temperature for one hour
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was then washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-5ec4298098fd442581c3383f9e90431e
Source dataset
uspto-grants-1995_07
Patent number
US05436257

Reaction notes

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