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

HRID 1909329Notes

Reaction equation

HRID 1909329 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-3a70af5183e6459fb3acd2a9a00375a4
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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