Methanol → 4-Nitro-2-(trifluoromethyl)anisole

HRID 28249

Reaction equation

HRID 28249 reaction equation
[OH-:1].[Na+].Cl[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[C:13]([F:16])([F:15])[F:14].O.[CH3:18]O>[Cl-].C([N+](CC)(CC)CC)C>[CH3:18][O:1][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[C:13]([F:16])([F:15])[F:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 612132-Chloro-5-nitrobenzotrifluoride

Product 1

HCID 695624-Nitro-2-(trifluoromethyl)anisoleYield 60.7%

Reagents, catalysts & solvents 1

HCID 5946Tetraethylammonium ChlorideCatalyst

Conditions

Temperature
30 °C

Procedure

45 g of sodium hydroxide and 10 g of tetraethylammonium chloride in 200 g of methanol are initially introduced, 112.5 g of 2-chloro-5-nitro-benzotrifluoride are added dropwise at 25° to 30° C. and the mixture is then stirred at 30° C. for a further 5 hours. The mixture is then poured into 250 ml of water and extracted with methylene chloride. After evaporating off the solvent, the compound is recrystallised from isopropanol. 67 g of 2-methoxy-5-nitro-benzotrifluoride with a melting point of 70° to 74° C. are obtained.

Workup

  1. extractionextracted with methylene chloride
  2. customAfter evaporating off the solvent
  3. customthe compound is recrystallised from isopropanol

Sources & evidence

ORD record
ord-ce9d6417b525447fad8a7a50888eda11
Source dataset
uspto-grants-1980_09
Patent number
US04225731

Linked notes

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