3-(Trifluoromethyl)phenol → 2-(3-(Trifluoromethyl)phenoxy)-3-pyridinecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence