3-Pyridinemethanol → 3-Pyridylmethyl (3-Trifluoromethylphenoxy)(4-chlorophenyl)acetate hydrochloride

Participants

Reaction Conditions

Reaction Steps

A solution of 3-pyridylcarbinol (5.7 g., 0.0522 mole) in triethylamine (144 ml., 0.13 mole) is cooled to -15° C. To this solution is added (3-trifluoromethylphenoxy)(4-chlorophenyl)acetyl chloride (18 g., 0.0515 mole) in ether (25 ml.). The reaction mixture is stirred for four hours at -5° C. and then at room temperature for 4 hours. The reaction mixture is filtered and the filtrate is washed successively with water, dilute sodium bicarbonate and then water until neutral. The ether solution is dried over magnesium sulfate filtered and to this solution is added ethanolic HCl. An oil separated which slowly crystallized. The solid is collected and recrystallized from a mixture of of isopropanol (30 ml.) and ether (30 ml.) to afford 8.6 g. of product. A small sample recrystallized for analysis has a melting point of 147°-149° C.

Provenance & Evidence