4'-(Trifluoromethyl)propiophenone

Chemical Properties

solid

Uses

4-(Trifluoromethyl)propiophenone is used as a reagent in the preparation of ketones and alcohols in organic synthesis. It is also used as a starting material for the synthesis of various compounds such as 4-(trifluoromethyl)phenylacetic acid, which is used as a building block in the synthesis of pharmaceuticals.

Synthesis

General procedure for the synthesis of 4-(trifluoromethyl)propiophenone from 1-(4-trifluoromethylphenyl)-1-propanol: First, a solution of 1-(4-trifluoromethylphenyl)-1-propanol prepared in step 1 was mixed with 3.9 kg of tetrabutylammonium hydrogensulphate and 12.3 kg of sodium dihydrogen phosphate dihydrate and dissolved in 32 L of deionized water. Subsequently, the mixture was washed with 10 L of deionized water, and then 318 kg of a 12% aqueous sodium perchlorate solution was added to the mixture, followed by washing the reaction mixture with 35 L of deionized water. The resulting solution was allowed to stand for 30 minutes before the organic layer was separated and mixed with 358 L of deionized water and 18 kg of 38% hydrochloric acid and stirred for 5 minutes. The organic layer was separated and washed with deionized water to finally obtain 378 kg of 4-(trifluoromethyl)propiophenone from the organic layer (yield: 97.2%).

References

[1] Synthetic Communications, 1989, vol. 19, # 9-10, p. 1735 - 1744
[2] Patent: WO2006/112565, 2006, A1. Location in patent: Page/Page column 16-17
[3] Journal of Medicinal Chemistry, 1995, vol. 38, # 20, p. 3918 - 3932
[4] European Journal of Medicinal Chemistry, 1995, vol. 30, # 1, p. 85 - 94
[5] Journal of Organic Chemistry, 2003, vol. 68, # 4, p. 1594 - 1596