Methanol → Methyl 4-(4-pyridinyl)benzoate

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (683 mL, 9358.59 mmol) was added dropwise over 20 minutes to a suspension of sodium 4-(pyridin-4-yl)benzoate (690 g, 3119.53 mmol) in methanol (15 L) at −10° C., keeping the temperature below 15° C. The mixture was stirred for 10 minutes then heated to 65° C. for 15 hours. The reaction mixture was cooled to 20° C. and the solvent was evaporated. The solid residue was partioned between ethyl acetate (14 L) and aqueous saturated sodium bicarbonate solution (14 L). The organic layer was separated and the aqueous layer extracted with ethyl acetate (7 L). The combined organics were washed with water (14 L), saturated brine (7 L) dried over magnesium sulfate, filtered and evaporated to dryness to afford methyl 4-(pyridin-4-yl)benzoate (570 g, 86%) as a solid.

Provenance & Evidence