3-(Trifluoromethyl)phenol → 2-(3-(Trifluoromethyl)phenoxy)-3-pyridinecarboxylic acid
Reaction equation
C[O-].[Na+].[F:4][C:5]([F:14])([F:13])[C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1.Cl[C:16]1[N:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([OH:20])=[O:19]>CO>[F:4][C:5]([F:13])([F:14])[C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=1)[O:12][C:16]1[N:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([OH:20])=[O:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 180 °C
Procedure
To a flask containing a solution of 45.4 grams (0.21 mole) 25% sodium methoxide in 100 milliliters of methanol were added 81.5 grams (0.5 mole) 3-trifluoromethylphenol and 15.8 grams (0.1 mole) 2-chloronicotinic acid. The reaction mass was heated and the methanol distilled off. The pot temperature was raised to 180° C. and held at that level for one hour. The mixture was then cooled to 100° C. and poured into 500 milliliters ice water. The aqueous mixture was extracted with 3 portions of 200 milliliters each, of diethyl ether, then acidified with glacial acetic acid. A solid precipitated, which was filtered, washed with water and dried, to give 25.8 grams (91.2% of theoretical yield) of 2-(3-trifluoromethylphenoxy)nicotinic acid, m.p. 149°-151° C.
Workup
- temperatureThe reaction mass was heated
- distillationthe methanol distilled off
- temperatureThe mixture was then cooled to 100° C.
- additionpoured into 500 milliliters ice water
- extractionThe aqueous mixture was extracted with 3 portions of 200 milliliters each, of diethyl ether
- customA solid precipitated
- filtrationwhich was filtered
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-7b3c66f2d5d449e7beb6100d4276f20d
- Source dataset
- uspto-grants-1981_02
- Patent number
- US04251263
Reaction notes
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