Sodium Iodide → HCID 18949794, compound

Participants

Reaction Steps

To 300 ml of acetonitrile were added 16.6 g (0.1 mole) of ethyl 4-hydroxybenzoate, 31.6 g (0.22 mole) of 1-bromo-2-chloroethane and 60.8 g of anhydrous potassium carbonate and the mixture was refluxed for 20 hours. The reaction mixture was then allowed to cool to room temperature and the solid matter was filtered off. The filtrate was concentrated under reduced pressure. To the resultant oily residue were added 15 g (0.1 mole) of sodium iodide and 50 g (0.3 mole) of triethyl phosphite and the mixture was stirred at 160° C. for 18 hours. The reaction mixture was then allowed to cool to room temperature, after which 50 ml of ethanol was added to the reaction mixture. While this mixture was stirred under ice-cooling, 100 ml of 2N aqueous sodium hydroxide solution was gradually added portionwise. The mixture was stirred at room temperature for 12 hours, at the end of which time 150 ml of water and 150 ml of chloroform were added. After phase separation, the water layer was separated. This aqueous solution was acidified with 150 ml of 4N hydrochloric acid and extracted with chloroform. The chloroform layer was washed with 200 ml of water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform-ethyl acetate=1:1) to provide 3.3 g of 4-[2-(diethoxyphosphoryl)ethoxy]benzoic acid as colorless crystals (m.p. 86°-88° C.).

Provenance & Evidence