Nitric Acid → 2-Methyl-3-nitro-5-(trifluoromethyl)benzoic acid

HRID 2208660Notes

Reaction equation

HRID 2208660 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+:15]([O-])([OH:17])=[O:16].O>OS(O)(=O)=O>[CH3:1][C:2]1[C:10]([N+:15]([O-:17])=[O:16])=[CH:9][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 27755852-Methyl-5-(trifluoromethyl)benzoic acid

Product 1

HCID 682955012-Methyl-3-nitro-5-(trifluoromethyl)benzoic acidYield 76%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a stirred solution of 2-methyl-5-(trifluoromethyl)benzoic acid (2.00 g, 9.80 mmol) in H2SO4 (20 mL, 12 N) was added HNO3 (2 mL, 12N) at 0° C. After stirring for 3 hours, water was added and resulting precipitate was collected. The solid was washed with water and dried to give the titled compound as a white solid (1.90 g, 76% yield). 1H-NMR (400 MHz, CDCl3) δppm; 8.43 (s, 1H), 8.15 (s, 1H), 2.77 (s, 3H); MS (ES) [M−H] 247.8.

Workup

  1. customresulting precipitate
  2. customwas collected
  3. washThe solid was washed with water
  4. customdried

Sources & evidence

ORD record
ord-79d683df2e284af1ba278b1e165f1ae5
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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