2-Chloroethanol → (4-Fluorophenyl)(4-(2-hydroxyethoxy)phenyl)methanone

Participants

Reaction Steps

In an oven-dried flask placed under a nitrogen atmosphere, 4-fluorophenyl-4-hydroxyphenyl methanone (100 g), 2-chloroethanol (75 g), potassium carbonate (134 g) and potassium iodide (11.5 g) were stirred in anhydrous dimethylformamide (400 mL) using a mechanical stirrer. The reaction mixture was heated to reflux for 4 hours. It was cooled to room temperature and then poured into a beaker containing deionized water (1 L) and ice. Concentrated hydrochloric acid was added while stirring vigorously until the pH reached 3. The mixture was transferred to a separatory funnel and then extracted with chloroform (2×600 mL). The organic layers were combined and washed with a saturated aqueous solution of sodium bicarbonate (750 mL), dried over sodium sulfate and concentrated by rotary evaporation to yield a solid. The solid was slurried in a minimal amount of a solution of 10% ethyl acetate/90% hexanes and collected by vacuum filtration. 120 grams of 4-fluorophenyl-4-(2-hydroxyethoxy)phenyl methanone was isolated.

Provenance & Evidence