Butyl iodide → 3-Butoxy-4-methoxybenzaldehyde

HRID 1068575Notes

Reaction equation

HRID 1068575 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:5]([OH:6])[CH:4]=1.[CH2:12](I)[CH2:13][CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH2:12]([O:6][C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][C:7]=1[O:8][CH3:9])[CH:2]=[O:1])[CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 12127Isovanillin

Product 1

HCID 5924713-Butoxy-4-methoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Isovanillin (6.00 g, 39.4 mM), butyl iodide (5.7 ml, 49.3 mM), and anhydrous potassium carbonate (6.8 g, 49.3 mM) were dissolved in dried dimethylformamide (50 ml) and stirred at room temperature for one night, then the solution was diluted with ethyl acetate (300 ml) and washed with water. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed in vacuo to obtain a residue as a light yellow oil. The residue was purified by flash chromatography (SiO2: eluted by 20% ethyl acetate/hexane solution). The solvent was removed in vacuo and the resultant product was dried to obtain 3-butoxy-4-methoxy-3-benzaldehyde 8.09 g (yield 99.0%) as a light yellow oil.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a2abfa3bef664394b6b93eed19078049
Source dataset
uspto-grants-2001_06
Patent number
US06251897B1

Reaction notes

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