Hydrochloric Acid → 3-Trifluoromethylcinnamic acid

Participants

Reaction Conditions

Reaction Steps

In an inert atmosphere, 3-(trifluoromethyl)benzaldehyde (13.26 g, 76.15 mmol) was dissolved in pyridine (58 ml) and malonic acid (15 g, 145 mmol) was added and the mixture was warmed to 50° C. followed by slow addition (over 5 minutes) of piperidine (5.8 ml, 58.6 mmol). The resulting suspension was warmed to 75° C. and stirring was continued for 3.5 h. The reaction mixture was cooled to 0° C. and poured onto an ice-cold solution of concentrated hydrochloric acid (12 M, 32 ml) in water (400 ml). The precipitated product was filtered off and dried at HV to give 14.21 g (68%) of 3-(3-trifluoromethyl-phenyl)-acrylic acid. LC-MS: tR=0.88 min; [M+H]+=no ionisation.

Provenance & Evidence