Potassium Carbonate → 3-Methoxy-4-propoxy-5-nitrobenzaldehyde

HRID 341857

Reaction equation

HRID 341857 reaction equation
[N+:1]([C:4]1[C:5]([OH:14])=[C:6]([O:12][CH3:13])[CH:7]=[C:8]([CH:11]=1)[CH:9]=[O:10])([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:21](I)[CH2:22][CH3:23]>CN(C)C=O>[CH3:13][O:12][C:6]1[CH:7]=[C:8]([CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=1[O:14][CH2:21][CH2:22][CH3:23])[CH:9]=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 811345-Nitrovanillin

Product 1

HCID 120806463-Methoxy-4-propoxy-5-nitrobenzaldehydeYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-nitrovanillin (19.72 g, 100 mmol), potassium carbonate (35 g, 253.23 mmol) and propyl iodide (32.86 mL, 335.83 mmol) in 160 mL of N,N-dimethylformamide was stirred at 60° C. for 12 hours. The mixture was then cooled, quenched with water and extracted with methylene chloride. The organic layer was washed several times with water, dried over magnesium sulfate, filtered and evaporated in vacuo to an oil which was purified by flash chromatography on silica gel (230-400 mesh) using 2:1 hexane/ethyl acetate as eluent, to provide 3-methoxy-4-propoxy-5-nitrobenzaldehyde (13.54 g, 57%). 1H NMR (CDCl3): 1.00 (t, 3H), 1.85 (m, 2H), 4.00 (s, 3H), 4.25 (t, 2H), 7.65 (s, 1H), 7.85 (s, 1H), 9.95 (s, 1H).

Workup

  1. temperatureThe mixture was then cooled
  2. customquenched with water
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed several times with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to an oil which
  8. customwas purified by flash chromatography on silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-7b2a21f1c1314b4aaf26a3090406351c
Source dataset
uspto-grants-1999_01
Patent number
US05856323

Linked notes

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