Sulfuric Acid → Ibuprofen trifluoroethyl ester

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence