Hydrochloric Acid → Ethyl 3-nitro-4-(trifluoromethyl)benzoate

HRID 257575Notes

Reaction equation

HRID 257575 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14])[C:7]([OH:9])=[O:8])([O-:3])=[O:2].Cl.[CH2:18](O)[CH3:19]>>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[C:13]([F:14])([F:15])[F:16])[C:7]([O:9][CH2:18][CH3:19])=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 27790153-Nitro-4-(trifluoromethyl)benzoic acid

Product 1

HCID 19783148Ethyl 3-nitro-4-(trifluoromethyl)benzoateYield 64%

Procedure

A solution of 555 mg (2.36 mmol) of 3-nitro-4-(trifluoromethyl)benzoic acid (from Step B) in 10 mL of ethanol was treated with 1 mL of concentrated hydrochloric acid. The solution was stirred at reflux for 2 days, then cooled, and partitioned between ethyl acetate and H2O. The organic layer was washed successively with saturated NaHCO3, H2O, and brine. The ethyl acetate solution was then dried over Na2SO4 and concentrated to give 400 mg (64%) of the title compound as a pale yellow foam, homogeneous by TLC in 4:1 hexane-EtOAc; mass spectrum (EI) m/e 263 (M+). 200 MHz 1H NMR (CDCl3) δ1.43 (t, J=7.2 Hz, 3H), 4.46 (q, J=7.2 Hz, 2H), 7.92 (d, J=8 Hz, 1H), 8.36 (d, J=8 Hz, 1H), 8.49 (s, 1H).

Workup

  1. temperatureat reflux for 2 days
  2. temperaturecooled
  3. custompartitioned between ethyl acetate and H2O
  4. washThe organic layer was washed successively with saturated NaHCO3, H2O, and brine
  5. dry with materialThe ethyl acetate solution was then dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3405e901a97141a080d0db29b9748383
Source dataset
uspto-grants-1993_11
Patent number
US05262412

Reaction notes

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