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

HRID 1854147Notes

Reaction equation

HRID 1854147 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 cone. H2SO4+0.1 mL of cone. 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-884374ea5b504213bac566c402b991cd
Source dataset
uspto-grants-2015_02
Patent number
US08962620B2

Reaction notes

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