Hydrochloric Acid → 2,6-Di(2-fluoroethoxy)benzoic acid

Participants

Reaction Steps

To a stirred solution of 3.0 grams (0.075 mole) of sodium hydroxide in 150 ml of ethanol was added 11.3 grams (0.039 mole) of 2-fluoroethyl 2,6-di(2-fluoroethoxy)benzoate (prepared by the method of Step A of Example 13 from 2,6-dihydroxybenzoic acid and three equivalents of 1-bromo-2-fluoroethane). The reaction mixture was stirred at room temperature for approximately 48 hours. The reaction mixture was filtered, and the filter cake was saved. The filtrate was evaporated under reduced pressure leaving a residue. The filter cake and residue were added to 200 ml of an aqueous, 10% hydrochloric acid solution. The resultant mixture was stirred at room temperature and was extracted with several portions of methylene chloride. The extracts were combined and dried over anhydrous magnesium sulfate. The dried organic phase was filtered, and the filtrate was evaporated under reduced pressure to yield 4.9 grams of 2,6-di(2-fluoroethoxy)benzoic acid as a solid, mp 57°-58° C.

Provenance & Evidence