3-Hydroxybenzyl alcohol → (3-((5-(Trifluoromethyl)pyridin-2-yl)oxy)phenyl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-trifluoromethyl-2-chloro-pyridine (150.0 g, 0.826 mol) in DMF (1.9 L) was added 3-hydroxy-phenyl-methanol (112.5 g, 0.906 mol) and of potassium carbonate (171.0 g, 1.237 mol). The solids were washed into the flask with 100 mL of DMF. The stirred mixture was heated to 95-105° C. for 5 h. It was cooled to ambient temperature and then poured into 5 L of stirred ice-water. The mixture was extracted with ether:hexane (2:1, 1.5 L, 1.0 L). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo to dryness to give the product (222.5 g, 100%).

Provenance & Evidence