1-Bromopropane → 3,4-Dipropoxybenzaldehyde

HRID 1169460Notes

Reaction equation

HRID 1169460 reaction equation
[CH:1](=[O:10])[C:2]1[CH:9]=[CH:8][C:6]([OH:7])=[C:4]([OH:5])[CH:3]=1.[CH2:11](Br)[CH2:12][CH3:13].[C:15](=O)([O-])[O-].[K+].[K+].C(O[CH2:25][CH3:26])(=O)C>CN(C)C=O>[CH2:11]([O:5][C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][C:6]=1[O:7][CH2:15][CH2:25][CH3:26])[CH:1]=[O:10])[CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 78401-BromopropaneHCID 87683,4-DihydroxybenzaldehydeHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

Product 1

HCID 41464793,4-Dipropoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To protocatechualdehyde (4.45 g) dissolved in dimethylformamide (65 ml) were added 1-propylbromide (9.91 g) and potassium carbonate (13.4 g), and the resulting mixture was stirred at room temperature for 19 hours. The reaction mixture was diluted with ethyl acetate, 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 concentration under reduced pressure to remove the solvent, the residue was subjected to purification using silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 3,4-dipropoxybenzaldehyde (6.72 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. concentrationAfter concentration under reduced pressure
  4. customto remove the solvent
  5. customthe residue was subjected to purification

Sources & evidence

ORD record
ord-65fac79dccd44c59bf2a4c7179d206da
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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