反应详情

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.

1. customIn an oven-dried flask placed under a nitrogen atmosphere
2. temperatureThe reaction mixture was heated
3. temperatureto reflux for 4 hours
4. additionpoured into a beaker
5. customThe mixture was transferred to a separatory funnel
6. extractionextracted with chloroform (2×600 mL)
7. washwashed with a saturated aqueous solution of sodium bicarbonate (750 mL)
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated by rotary evaporation
10. customto yield a solid
11. filtrationcollected by vacuum filtration