Sulfuric Acid → p-Isobutylphenylacetic acid-2,2,2-trifluoroethyl ester

HRID 26463Notes

Reaction equation

HRID 26463 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+].[F:26][C:27]([F:31])([F:30])[CH2:28]O>>[F:26][C:27]([F:31])([F:30])[CH2:28][O:13][C:12](=[O:14])[CH2:11][C:8]1[CH:7]=[CH:6][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 64092,2,2-TrifluoroethanolHCID 10340Sodium CarbonateHCID 15250Ibufenac

Product 1

HCID 21323305p-Isobutylphenylacetic acid-2,2,2-trifluoroethyl ester

Procedure

A mixture of 1.9 g of p-isobutylphenylacetic acid, 10 ml of 2,2,2-trifluoroethanol and 1 ml of concentrated sulfuric acid was refluxed for 5 hours. After the reaction was complete, the mixture was poured into ice-water. The resulting mixture was neutralized with adding 5% sodium carbonate solution, and then extracted with ether. The ether layer separated was dehydrated and concentrated to leave an oily residue. The residue was distilled in vacuo to yield 2.3 g of p-isobutylphenylacetic acid-2,2,2-trifluoroethyl ester as a colorless liquid, boiling at 78°-79° C./1 mmHg. Analysis-Calculated for C14H17F3O2 : C, 61.30; H, 6.25. Found: C, 61.01; H, 6.15. Mass spectrum: parent ion 274 m/e.

Workup

  1. temperaturewas refluxed for 5 hours
  2. extractionextracted with ether
  3. customThe ether layer separated
  4. concentrationconcentrated
  5. customto leave an oily residue
  6. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-b2e501a44b29474a8101c5558508fdb5
Source dataset
uspto-grants-1979_04
Patent number
US04150137

Reaction notes

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