Ethanol → Ethyl 3-nitro-4-(trifluoromethyl)benzoate

HRID 1361663

Reaction equation

HRID 1361663 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].S(=O)(=O)(O)O.[CH2:22](O)[CH3:23]>C(OCC)(=O)C.O>[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][CH2:22][CH3:23])=[O:8])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 27790153-Nitro-4-(trifluoromethyl)benzoic acid

Product 1

HCID 19783148Ethyl 3-nitro-4-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Nitro-4-(trifluoromethyl)benzoic acid (10 g, 43 mmol) was taken up in 100 ml of ethanol and sulfuric acid (11 ml) was added to the mixture. The reaction was heated to reflux for 12 hours. The volatiles were removed in vacuo. The residue obtained was diluted with ethyl acetate and water. The layers were separated and the organic layer was washed with an aqueous solution of saturated sodium bicarbonate, water and brine. The organic layer was then dried with sodium sulfate and the volatiles removed in vacuo to give ethyl 3-nitro-4-(trifluoromethyl)benzoate a clear yellow oil.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 12 hours
  3. customThe volatiles were removed in vacuo
  4. customThe residue obtained
  5. customThe layers were separated
  6. washthe organic layer was washed with an aqueous solution of saturated sodium bicarbonate, water and brine
  7. dry with materialThe organic layer was then dried with sodium sulfate
  8. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-239bb387f3e949059ac6268ec44f034b
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Linked notes

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