Water → 3,4-Dimethoxy-5-nitrobenzaldehyde

HRID 341852

Reaction equation

HRID 341852 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-199b9efcfdb54d4e868c96008a8f708e
Source dataset
uspto-grants-1999_01
Patent number
US05856323

Linked notes

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