Methanol → Methyl 3-nitro-5-(trifluoromethyl)benzoate

HRID 391410Notes

Reaction equation

HRID 391410 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7]([OH:9])=[O:8])([O-:3])=[O:2].[CH3:17]O>>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=1)[C:7]([O:9][CH3:17])=[O:8])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 887MethanolHCID 6166023-Nitro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 18942157Methyl 3-nitro-5-(trifluoromethyl)benzoateYield 88%

Procedure

3-Nitro-5-(trifluoromethyl)benzoic acid (25.0 g, 106.3 mmol) was dissolved in methanol (60 mL) which was bubbled with hydrochloric acid gas for 1 h. The reaction was allowed to stir at room temperature overnight and concentrated. The crude product was dissolved in ethyl acetate, washed with water (2×), brine (2×) dried over sodium sulfate and concentrated. Flash chromatography on silica gel afforded 23.4 g (88%) of the desired compound. 1H-NMR (CDCl3, 500 MHz) δ 9.02 (s, H), 8.66 (s, 1H), 8.61 (s, 1H), 4.03 (s, 3H).

Workup

  1. customwas bubbled with hydrochloric acid gas for 1 h
  2. concentrationconcentrated
  3. dissolutionThe crude product was dissolved in ethyl acetate
  4. washwashed with water (2×), brine (2×)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0cf66fe26f434207a5602f8cd5c2609b
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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