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

HRID 1030694Notes

Reaction equation

HRID 1030694 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[O:10])=[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]=[CH:7][C:6]([CH:9]=[O:10])=[CH:5][C:4]=1[O:11][CH2:21][O:22][CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 12127IsovanillinHCID 81531Diisopropylethylamine

Product 1

HCID 6401524-methoxy-3-(methoxymethoxy)benzaldehydeYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

In 100 ml of dimethylformamide was dissolved 10 g of isovaniline, and 14 ml of N,N-diisopropylethylamine was added to the solution and the mixture was stirred. The liquid mixture was cooled to 0° C. and 7.2 ml of chloromethyl methyl ether was added to the mixture, and 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, washed with water and dried. Removal of the solvent by distillation gave 11.0 g (yield=85%) of 4-methoxy-3-methoxymethoxybenzaldehyde in the form of a yellow oil.

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. washwashed with water
  7. customdried
  8. customRemoval of the solvent
  9. distillationby distillation

Sources & evidence

ORD record
ord-53b157f9d8434a349a565b491ce76373
Source dataset
uspto-grants-1992_04
Patent number
US05106871

Reaction notes

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