Description
3-(3-Trifluoromethylphenyl)propionic acid is an important organic solvent with a mild, pleasant aroma, used as an efficient organic reagent in polymer production processes and as a co-catalyst for trifluoroacetic acid. It is used in biological research as a substrate for the synthesis of various compounds and for the study of enzyme-catalysed reactions. It is also used in the synthesis of cinacalcet. Cinacalcet is a drug used to treat chronic kidney disease (dialysis) and high levels of calcium in the blood (parathyroid disease).
Chemical Properties
3-(3-Trifluoromethylphenyl)propionic acid has the appearance of a white or colourless to yellowish powder to a lumpy to clear liquid with a melting point of 35 °C and a boiling point of 149 °C/11 mmHg; store at room temperature.
Uses
3-(3-Trifluoromethylphenyl)propionic Acid can be used as catalysts.
Uses
3-(3-Trifluoromethylphenyl)propionic acid is used in the synthesis of Cinacalcet and also participates in the boron-catalyzed N-alkylation of amines of carboxylic acids.
Preparation
3-(3-Trifluoromethylphenyl)propionic acid is synthesised by the reaction of 3-trifluoromethylaniline and propionic acid.
Synthesis
Preparation of 3-(3-trifluoromethylphenyl)propionic acid: 3-Trifluoromethylcinnamic acid (0.463 mol, 100 g) was dissolved in 1.0 L of methanol and transferred to a hydrogenation reactor. 5% Pd/C catalyst (3 g) was added. The hydrogenation reaction was carried out at 1 kg/cm2 Hpressure and 250 °C for about 10 hours. Upon completion of the reaction, the reaction mixture was filtered and the catalyst was washed with methanol (100 mL). The filtrate was distilled under reduced pressure to remove the methanol to give 3-(3-trifluoromethylphenyl)propionic acid as crude product (100 g, 100% yield).
References
[1] Patent: WO2010/100429, 2010, A1. Location in patent: Page/Page column 19
[2] Patent: WO2008/117299, 2008, A1. Location in patent: Page/Page column 16
[3] Beilstein Journal of Organic Chemistry, 2012, vol. 8, p. 1366 - 1373
[4] Patent: US2009/99228, 2009, A1. Location in patent: Page/Page column 10-11; 18
[5] Patent: EP2013209, 2011, B1. Location in patent: Page/Page column 22
