2-Chloro-5-nitrobenzaldehyde → Benzaldehyde, 2-methoxy-5-nitro-

HRID 840601Notes

Reaction equation

HRID 840601 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:13][O-:14].[Na+]>CO>[CH3:13][O:14][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

4

Reactant 2

HCID 729332-Chloro-5-nitrobenzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 90685Benzaldehyde, 2-methoxy-5-nitro-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2.5 grams (13.5 mmol) of 2-chloro-5-nitrobenzaldehyde (Aldrich Chem. Co.) in 250 mL of CH3OH was treated with 2.92 grams (54.1 mmol) of sodium methoxide, refluxed for 16 hours and allowed to cool to room temperature. After removal of the solvent in vacuo, the residue was suspended in water, treated with 2N HCl (adjusting to pH<5) and extracted into methylene chloride. After drying over MgSO4, the solvent was removed in vacuo to give a yellow solid, 2.02 grams (83%).

Workup

  1. temperaturerefluxed for 16 hours
  2. customAfter removal of the solvent in vacuo
  3. additiontreated with 2N HCl (adjusting to pH<5)
  4. extractionextracted into methylene chloride
  5. dry with materialAfter drying over MgSO4
  6. customthe solvent was removed in vacuo
  7. customto give a yellow solid, 2.02 grams (83%)

Sources & evidence

ORD record
ord-df2cbe0415044cf793849a43e12d4722
Source dataset
uspto-grants-2002_04
Patent number
US06369074B1

Reaction notes

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