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

HRID 1030693Notes

Reaction equation

HRID 1030693 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(CC)C(C)C)(C)C.[CH3:21][O:22][CH2:23]Cl.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[O:11][CH2:21][O:22][CH3:23])[CH:9]=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 1183VanillinHCID 7864Chloromethyl Methyl EtherHCID 81531Diisopropylethylamine

Product 1

HCID 796613-Methoxy-4-(methoxymethoxy)benzaldehydeYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

In 320 ml of dimethylformamide was dissolved 3.2 g of vaniline, and 44.8 g of N,N-diisopropylethylamine was added to the solution and the mixture was stirred. The liquid mixture was cooled to 0° C. and 18.1 ml of chloromethyl methyl ether was added to the liquid mixture. The temperature was elevated to room temperature and the mixture was stirred for 5 hours. After the reaction, a large quantity of water was added to the reaction mixture, and the mixture was extracted with diethyl ether and the solvent was removed from the extract by distillation. The obtained residue was allowed to stand under ice cooling, and the obtained solid was washed with petroleum ether and recovered by filtration to obtain 34.0 g (yield=83%) of intended 3-methoxy-4-methoxymethoxybenzaldehyde.

Workup

  1. additionwas added to the solution
  2. customwas elevated to room temperature
  3. stirringthe mixture was stirred for 5 hours
  4. customAfter the reaction
  5. extractionthe mixture was extracted with diethyl ether
  6. customthe solvent was removed from the
  7. extractionextract by distillation
  8. washthe obtained solid was washed with petroleum ether
  9. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-35958c812d9b428c8a3a8dace5bc1ec2
Source dataset
uspto-grants-1992_04
Patent number
US05106871

Reaction notes

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