Hydrochloric Acid → 2-(4-(Trifluoromethyl)phenyl)propanoic acid

反応式

[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:15])[C:10]([O:12]CC)=[O:11])=[CH:5][CH:4]=1.[OH-].[Na+].Cl>C(O)C>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH3:15])[C:10]([OH:12])=[O:11])=[CH:7][CH:8]=1

参加物

実験手順

A mixture of 1.93 g (7.8 mmol) of ethyl 2-(4-[trifluoromethyl]phenyl)propionate, 10 mL of 1N NaOH, and 10 mL of absolute ethanol was heated to reflux for 3 hours, allowed to cool to room temperature, and poured into 50 mL of 1N HCl. The resulting aqueous mixture was extracted with three 10 mL portions of dichloromethane. Combination, drying (MgSO4), and concentration of the organic layers afforded an oil which was crystallized from hexanes to give 0.90 g (50% yield) of the acid as a white, crystalline solid: mp 56°-58° C.; 1H NMR (CDCl3) 1.47 (d, 3H, J=7 Hz), 3.73 (q, 1H, J=7 Hz), 7.36 (d, 2H, J=8 Hz), 7.52 (d, 2H, J=8 Hz); 19F NMR (CDCl3, relative to CFCl3)-63.2 ppm (s); IR (neat) 2963, 1712, 1619, 1419, 1327, 1264, 1232, 1166, 1124, 1072, 1019, 843 cm-1.