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

HRID 1501700Notes

Reaction equation

HRID 1501700 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]>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

4

Reactant 2

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

Product 1

HCID 682955012-Methyl-3-nitro-5-(trifluoromethyl)benzoic acidYield 60%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A stirred solution of 2-methyl-5-(trifluoromethyl)benzoic acid (1 mmol) in conc. H2SO4 (2 mL) was cooled to −10° C. and a nitrating mixture (0.4 mL of conc. H2SO4+0.1 mL of conc. HNO3) was added to it in dropwise manner. The reaction mixture was stirred at same temperature for 20 min before warming to room temperature. The resulting precipitate was filtered off and dried to obtain 2-methyl-3-nitro-5-(trifluoromethyl)benzoic acid which was used in next step without further purification (yield 60-70%).

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. customdried

Sources & evidence

ORD record
ord-293bf5308d6c40819346398e7910b34f
Source dataset
uspto-grants-2015_12
Patent number
US09206157B2

Reaction notes

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