Trifluoroacetic acid → 4,5-Dimethyl-2-nitrophenol

HRID 377936Notes

Reaction equation

HRID 377936 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].FC(F)(F)C(O)=O.[N:17]([O-:19])=[O:18].[Na+]>O>[CH3:8][C:7]1[C:2]([CH3:1])=[CH:3][C:4]([OH:9])=[C:5]([N+:17]([O-:19])=[O:18])[CH:6]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 72493,4-DimethylphenolHCID 23668193Sodium Nitrite

Product 1

HCID 3491174,5-Dimethyl-2-nitrophenolYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3,4-dimethylphenol(12.1 g, 0.1 mol), trifluoroacetic acid(250 ml) was added, and in water bath sodium nitrite(12.4 g, 0.18 mol) was added slowly. The resulting mixture was stirred at room temperature for 14 hours and concentrated under the reduced pressure to remove trifluoroacetic acid, followed by addition of water(150 ml), extracted with ether and purified by column chromatography to obtain the titled compound.

Workup

  1. concentrationconcentrated under the reduced pressure
  2. customto remove trifluoroacetic acid
  3. additionfollowed by addition of water(150 ml)
  4. extractionextracted with ether
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-0b0e5443759d41dcb892401eb1169ad5
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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