Dimethylformamide → 3,4-Diethoxybenzaldehyde

HRID 1169502Notes

Reaction equation

HRID 1169502 reaction equation
[CH:1](=[O:10])[C:2]1[CH:9]=[CH:8][C:6](O)=[C:4]([OH:5])[CH:3]=1.I[CH2:12][CH3:13].[C:14](=[O:17])([O-])[O-].[K+].[K+].[CH3:20]N(C=O)C>C(OCC)(=O)C>[CH2:12]([O:5][C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][C:6]=1[O:17][CH2:14][CH3:20])[CH:1]=[O:10])[CH3:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 748473,4-Diethoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To protocatechualdehyde (5.15 g) dissolved in DMF (70 ml) were added iodoethane (14.5 g) and potassium carbonate (15.5 g), and the resulting mixture was stirred at room temperature for 17.5 hours. The reaction mixture was diluted with ethyl acetate and washed respectively with water, a 1 N aqueous solution of sodium hydroxide, water and an aqueous saturated solution of sodium chloride, and the organic layer was dried with anhydrous magnesium sulfate. After evaporation under reduced pressure to remove the solvent, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 3,4-diethoxybenzaldehyde (6.73 g) as a yellow oil.

Workup

  1. washwashed respectively with water
  2. dry with materiala 1 N aqueous solution of sodium hydroxide, water and an aqueous saturated solution of sodium chloride, and the organic layer was dried with anhydrous magnesium sulfate
  3. customAfter evaporation under reduced pressure
  4. customto remove the solvent
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-ba54135951ce41eb9b5e273d42c5804f
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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