Water → Benzaldehyde, 2-methoxy-5-nitro-

HRID 1604733Notes

Reaction equation

HRID 1604733 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5].IC.[C:15](=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O>[CH3:15][O:1][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

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 668085-Nitrosalicylaldehyde

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Hydroxy-5-nitrobenzaldehyde (2.40 g, 14.0 mmol) was dissolved in dimethylformamide (50 mL). To this was added iodomethane (4.48 ml, 72.0 mmol) and sodium carbonate (3.04 g, 28.0 mmol). This mixture was stirred for 24 hours and was poured into water. The solid was collected by filtration to give 2.38 g (93.0%). Mp 88-89° C.;1H NMR (CDCl3): d, 10.46 (s,1H), 8.69 (d,1H), 8.45 (dd,1H), 7.15 (d,1H), 4.10 (s,3H). MS (DCl): 182 (MH+). C8H7NO4.

Workup

  1. filtrationThe solid was collected by filtration
  2. customto give 2.38 g (93.0%)

Sources & evidence

ORD record
ord-834a20921b8a4b1a88e8bfaeecc946d4
Source dataset
uspto-grants-1999_11
Patent number
US05994563

Reaction notes

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