Water → 3-Methoxy-4-propoxy-5-nitrobenzaldehyde

HRID 1647744Notes

Reaction equation

HRID 1647744 reaction equation
[H-].[Na+].[N+:3]([C:6]1[C:7]([OH:16])=[C:8]([O:14][CH3:15])[CH:9]=[C:10]([CH:13]=1)[CH:11]=[O:12])([O-:5])=[O:4].[CH2:17](I)[CH2:18][CH3:19].O>CN(C)C=O>[CH3:15][O:14][C:8]1[CH:9]=[C:10]([CH:13]=[C:6]([N+:3]([O-:5])=[O:4])[C:7]=1[O:16][CH2:17][CH2:18][CH3:19])[CH:11]=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 811345-Nitrovanillin

Product 1

HCID 120806463-Methoxy-4-propoxy-5-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of sodium hydride (6.09 g, 152.3 mmol) in 20 mL of dry dimethylformamide (DMF) was cooled to 0° C. and then 5-nitrovanillin (25 g, 126.8 mmol) in 41 mL of DMF was added dropwise. After 30 minutes, propyl iodide (25.87 g, 152.0 mmol) was added dropwise at 0° C. When the addition was completed, the reaction was maintained at room temperature for 2 hours and then stirred overnight at 70° C. Water was added, and the solution extracted with ethyl ether, washed with 10% NaOH, dried over MgSO4, filtered and then evaporated in vacuo to an oil (19 g, 62.7%).

Workup

  1. additionWhen the addition
  2. temperaturethe reaction was maintained at room temperature for 2 hours
  3. extractionthe solution extracted with ethyl ether
  4. washwashed with 10% NaOH
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo to an oil (19 g, 62.7%)

Sources & evidence

ORD record
ord-f33cdadce14f4ecf9c1080284b06d29d
Source dataset
uspto-grants-1995_07
Patent number
US05434151

Reaction notes

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