Sulfuric Acid → Ibuprofen trifluoroethyl ester

HRID 26451

Reaction equation

HRID 26451 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:15])[C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[F:16][C:17]([F:21])([F:20])[CH2:18]O.S(=O)(=O)(O)O>>[F:16][C:17]([F:21])([F:20])[CH2:18][O:13][C:12](=[O:14])[CH:11]([C:8]1[CH:7]=[CH:6][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:10][CH:9]=1)[CH3:15]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 3672Ibuprofen, (+-)-HCID 64092,2,2-Trifluoroethanol

Product 1

HCID 21323312Ibuprofen trifluoroethyl ester

Conditions

Temperature
100 °C

Procedure

A mixture of 4.12 g of 2-(p-isobutylphenyl)propionic acid, 15 ml of 2,2,2-trifluoroethyl alcohol and 4.9 g of concentrated sulfuric acid was heated at 100° C. for 12 hours. After the reaction was complete, the mixture was poured into ice-water and the resulting mixture was extracted with ether. The ether layer separated was washed sufficiently with successive 5% sodium carbonate solution and water, and dehydrated. The ether was removed by distillation to give an oily product. Distillation of the product in vacuo yielded 4.95 g of 2-(p-isobutylphenyl)propionic acid-2,2,2-trifluoroethyl ester as a pale yellow oil, boiling at 73°-74° C./0.12 mmHg. Analysis-Calculated for C15H19F3O2 : C, 62.48; H, 6.64. Found: C, 62.31; H, 6.61.

Workup

  1. extractionthe resulting mixture was extracted with ether
  2. customThe ether layer separated
  3. washwas washed sufficiently with successive 5% sodium carbonate solution and water
  4. customThe ether was removed by distillation
  5. customto give an oily product
  6. distillationDistillation of the product in vacuo

Sources & evidence

ORD record
ord-5b3df567dc5540b0be2bfd4e4aef4c7d
Source dataset
uspto-grants-1979_04
Patent number
US04150137

Linked notes

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