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-oxy)-ethanol in 100 ml of dry toluene, and 17.9 g (0.15 mole) of thionyl chloride were then added dropwise at 3°-15° C. The mixture was stirred for 1 day at 40° C. and for a further 8 hours at 70° C. and 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 and 50 ml of 1 N sodium hydroxide solution in succession and finally with 100 ml of water, and was dried and concentrated. The solid residue was stirred with 40 ml of petroleum ether at +3° C. (ice-bath) for 30 minutes, filtered off with suction, washed with a little cold petroleum ether and dried. 22.8 g of 1-chloro-2-(7-chlorodibenzofuran-3-oxy)-ethane were obtained as colorless crystals of melting point 105°-107° C.; yield: 81% of theory.

Provenance & Evidence