Nitric Acid → 4-Hydroxy-3-nitro-5-trifluoromethyl-benzoic acid methyl ester

HRID 641312Notes

Reaction equation

HRID 641312 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][O:6][C:7](=[O:19])[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:9]=1>C(O)(=O)C>[CH3:5][O:6][C:7](=[O:19])[C:8]1[CH:9]=[C:10]([C:15]([F:18])([F:17])[F:16])[C:11]([OH:14])=[C:12]([N+:1]([O-:4])=[O:2])[CH:13]=1

Participants

4

Reactant 2

HCID 944Nitric Acid2×HCID 13962148Methyl 4-hydroxy-3-(trifluoromethyl)benzoate

Product 1

HCID 667892374-Hydroxy-3-nitro-5-trifluoromethyl-benzoic acid methyl esterYield 99.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

65% aq. nitric acid solution (1.76 mL, 39 mmol) and fuming nitric acid (3.25 mL, 78 mmol) were added at −10° C. to a solution of 4-hydroxy-3-trifluoromethyl-benzoic acid methyl ester (4.31 g, 19.6 mmol) in acetic acid (54 mL). The ice bath was removed and the solution was stirred at room temperature for 5 h, then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated to afford 4-hydroxy-3-nitro-5-trifluoromethyl-benzoic acid methyl ester (5.16 g, 99%). Orange solid, MS (ISP)=263.9 (M−H)−.

Workup

  1. customThe ice bath was removed
  2. custompartitioned between water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-00d6997f6e844fc8aed8b5d681a76d19
Source dataset
uspto-grants-2010_04
Patent number
US07696200B2

Reaction notes

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