Methyl iodide → 2-Chloro-1-methoxy-3-methyl-4-nitrobenzene

HRID 1898991Notes

Reaction equation

HRID 1898991 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][C:3]=1[OH:12].[H-].[Na+].[CH3:15]I>CN(C=O)C>[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][C:3]=1[O:12][CH3:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 131473552-Chloro-3-methyl-4-nitrophenol

Product 1

HCID 137023832-Chloro-1-methoxy-3-methyl-4-nitrobenzeneYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-3-methyl-4-nitrophenol (9.39 g, 50.0 mmol) was reacted with sodium hydride (50%, 2.64 g, 55.0 mmol) and methyl iodide (7.81 g, 55.0 mmol) in dry DMF (200 ml) by the method described in 1 (a). After treatment with water, the product was extracted with chloroform, and the dried extract evaporated to dryness, leaving an oil which crystallised on cooling, leaving solid 2-chloro-3-methyl-4-nitroanisole (8.19 g).

Workup

  1. extractionAfter treatment with water, the product was extracted with chloroform
  2. extractionthe dried extract
  3. customevaporated to dryness
  4. customleaving an oil which
  5. customcrystallised
  6. temperatureon cooling

Sources & evidence

ORD record
ord-7a595a9bb28245488bfb0cabff633f57
Source dataset
uspto-grants-1996_11
Patent number
US05571833

Reaction notes

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