Hydrochloric Acid → 3-Trifluoromethylcinnamic acid
Reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].N1CCCCC1.Cl>N1C=CC=CC=1.O>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:14][C:15]([OH:17])=[O:16])[CH:8]=[CH:9][CH:10]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
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.
Workup
- temperatureThe resulting suspension was warmed to 75° C.
- temperatureThe reaction mixture was cooled to 0° C.
- filtrationThe precipitated product was filtered off
- customdried at HV
Sources & evidence
- ORD record
- ord-fd21d1fe407648c0a0d5339f1a0560e8
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834028B2
Reaction notes
Loading…