Methyl iodide → Benzaldehyde, 2-methoxy-5-nitro-

HRID 356633

Reaction equation

HRID 356633 reaction equation
[N+:1]([C:4]1[CH:11]=[C:8]([CH:9]=[O:10])[C:7]([OH:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:15]I>CN(C=O)C>[CH3:15][O:12][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][C:8]=1[CH:9]=[O:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 668085-Nitrosalicylaldehyde

Product 1

HCID 90685Benzaldehyde, 2-methoxy-5-nitro-Yield 87.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-nitrosalicylaldehyde (1.00 g, 6.0 mmol) in DMF (20 ml) was added NaH (246 mg) and methyl iodide (2.56 g, 18 mmol) at 0° C. The mixture was stirred for 8.5 hr at 60° C. After the reaction mixture was extracted with ether, the extract was washed with aqueous NaHCO3, brine and 5%-HCl/aq.NaCl, dried over MgSO4 and concentrated in vacuo to afford 2-methoxy-5-nitrobenzaldehyde (0.95 g, 87.8%) as a yellow needle.

Workup

  1. extractionAfter the reaction mixture was extracted with ether
  2. washthe extract was washed with aqueous NaHCO3, brine and 5%-HCl/aq
  3. dry with materialNaCl, dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8440ac320f3c4bc1ae9c1be85bec0d5e
Source dataset
uspto-grants-1998_11
Patent number
US05837711

Linked notes

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