Methyl iodide → 2,3-Dimethoxy-6-nitrobenzaldehyde

HRID 1154560Notes

Reaction equation

HRID 1154560 reaction equation
[H-].[Na+].[OH:3][C:4]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]([N+:14]([O-:16])=[O:15])[C:5]=1[CH:6]=[O:7].[CH3:17]I>CN(C)C=O>[CH3:17][O:3][C:4]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]([N+:14]([O-:16])=[O:15])[C:5]=1[CH:6]=[O:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2622422-Hydroxy-3-methoxy-6-nitrobenzaldehyde

Product 1

HCID 71721272,3-Dimethoxy-6-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A slurry of NaH (16.0 g, 50% oily dispersion, 337 mM) in dimethylformamide (200 ml) was treated dropwise with a solution of 2-hydroxy-3-methoxy-6-nitrobenzaldehyde (49.0 g, 248 mM) in DMF (300 ml) at such a rate that the temperature did not exceed 35° C. The mixture is aged at room temperature for 1 hour and then a large excess of methyl iodide (100 ml) is added dropwise. A slight exothermic reaction occurs. The mixture is then stirred vigorously for 19 hours at room temperature. After the removal of excess methyl iodide, the reaction mixture is poured into ice-water (1 l). The crude product, a brown solid, is filtered, washed with cold water, and then recrystallized from isopropyl alcohol (700 ml) to afford the product as a tan solid; yield 27.9 g (53.3%); m.p. 106°-108° C.

Workup

  1. customdid not exceed 35° C
  2. customA slight exothermic reaction
  3. customAfter the removal of excess methyl iodide
  4. additionthe reaction mixture is poured into ice-water (1 l)
  5. filtrationThe crude product, a brown solid, is filtered
  6. washwashed with cold water
  7. customrecrystallized from isopropyl alcohol (700 ml)

Sources & evidence

ORD record
ord-51c8f27b46654501a7d4ee5705d6435c
Source dataset
uspto-grants-1984_12
Patent number
US04490374

Reaction notes

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