Water → 3,4-Dimethoxy-5-nitrobenzaldehyde

HRID 1708443Notes

Reaction equation

HRID 1708443 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].[CH3:17]I.O>CN(C=O)C>[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][CH3:17])[CH:11]=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 811345-Nitrovanillin

Product 1

HCID 108675653,4-Dimethoxy-5-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of sodium hydride (4.87 g, 121.7 mmole) in 18 mL dry DMF was cooled to 0° C. and then 5-nitrovanillin (20 g, 101.4 mmole) in 30 mL of DMF was added dropwise. After 30 minutes, methyl iodide (43.18 g, 304.2 mmole) was added dropwise at 0° C. When the addition was completed, the mixture was warmed to room temperature and stirred overnight. Water was added and the solution extracted with ethyl ether, the organic layer was washed with 10% NaOH solution, dried over MgSO4, filtered and evaporated in vacuo to an oil (8.7 g, 40.7%).

Workup

  1. additionWhen the addition
  2. temperaturethe mixture was warmed to room temperature
  3. extractionthe solution extracted with ethyl ether
  4. washthe organic layer was washed with 10% NaOH solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo to an oil (8.7 g, 40.7%)

Sources & evidence

ORD record
ord-58e27ef2934542de83a283a8e938733f
Source dataset
uspto-grants-1994_10
Patent number
US05358938

Reaction notes

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