Ethylvanillin → 3-Ethoxy-4-(2-hydroxyethoxy)benzaldehyde

HRID 1066589Notes

Reaction equation

HRID 1066589 reaction equation
Br[CH2:2][CH2:3][OH:4].C(=O)([O-])[O-].[K+].[K+].[CH2:11]([O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[OH:22])[CH:17]=[O:18])[CH3:12]>CN(C=O)C>[CH2:11]([O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:21]=1[O:22][CH2:2][CH2:3][OH:4])[CH:17]=[O:18])[CH3:12]

Participants

5

Reactant 3

HCID 8467EthylvanillinHCID 108982-BromoethanolHCID 11430Potassium Carbonate

Product 1

HCID 17579533-Ethoxy-4-(2-hydroxyethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

2.76 ml of 2-bromoethanol and 5.40 g of potassium carbonate were added to a solution of 5 g of 3-ethoxy-4-hydroxybenzaldehyde in 150 ml of DMF. The reaction mixture was heated to 70° C. overnight and subsequently to 120° C. for a further 4 hrs. Then, the mixture was left to cool to room temperature, filtered and concentrated in a high vacuum. The crude product was isolated by extraction and purified by chromatography on silica gel. There were obtained 6.09 g of 3-ethoxy-4-(2-hydroxy-ethoxy)-benzaldehyde as a white solid.

Workup

  1. waitThen, the mixture was left
  2. temperatureto cool to room temperature
  3. filtrationfiltered
  4. concentrationconcentrated in a high vacuum
  5. customThe crude product was isolated by extraction
  6. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-432be3fd61474c40a94a443c764835b0
Source dataset
uspto-grants-2001_06
Patent number
US06242644B1

Reaction notes

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