alpha,alpha,alpha-Trifluoro-3,5-dinitrotoluene → 3-Methoxy-5-nitrobenzotrifluoride

HRID 873078Notes

Reaction equation

HRID 873078 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=1)([O-:3])=[O:2].[CH3:17][O-:18].[Na+]>CO>[CH3:17][O:18][C:6]1[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

4

Reactant 2

HCID 123060alpha,alpha,alpha-Trifluoro-3,5-dinitrotolueneHCID 10942334Sodium Methoxide

Product 1

HCID 5205973-Methoxy-5-nitrobenzotrifluorideYield 90.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 1,3-dinitro-5-(trifluoromethyl)benzene (10 g, 42.4 mmol) in absolute methanol (100 mL) was added sodium methanolate (3.43 g, 63.5 mmol) in absolute methanol (20 mL). The red alcoholic solution was refluxed for 1 h, then concentrated to remove solvent, diluted with ethyl acetate (80 mL) and water (30 mL). Separated organic part was dried over Na2SO4, filtered and concentrated to get the title product (8.5 g) as a red solid

Workup

  1. temperatureThe red alcoholic solution was refluxed for 1 h
  2. concentrationconcentrated
  3. customto remove solvent
  4. additiondiluted with ethyl acetate (80 mL) and water (30 mL)
  5. dry with materialSeparated organic part was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cfe8de0e60a24d389781e55e92e566a2
Source dataset
uspto-grants-2015_03
Patent number
US08975400B2

Reaction notes

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