Pyridine → 1-Chloro-2-(7-chlorodibenzofuran-3-oxy)-ethane

Participants

Reaction Conditions

Reaction Steps

11.9 g (0.15 mole) of pyridine were added to a suspension of 26.2 g (0.1 mole) of 2-(7-chlorodibenzofuran-3-yloxy)-ethanol in 100 ml of dry toluene, and 17.9 g (0.15 mole) of thionyl chloride were then added dropwise at from 3° to 15° C. The mixture was stirred for 1 day at 40° C. and for a further 8 hours at 70° C., after which it was cooled and 150 ml of toluene and 200 ml of ice water were added. The organic layer was washed with 100 ml of water, 50 ml of hydrochloric acid, 50 ml of 1N sodium hydroxide solution and 100 ml of water in succession, and was dried and evaporated down. The solid residue was stirred for 30 minutes with 40 ml of petroleum ether at +3° C. (ice bath), and was then filtered off under suction, washed with a little cold petroleum ether and dried. 22.8 g (81% of theory) of 1-chloro-2-(7-chlorodibenzofuran-3-yloxy)-ethane were obtained at colorless crystals of melting point 105°-107° C.

Provenance & Evidence