反应详情

To a solution of 1-(2,4-dihydroxy-3-propyl phenyl) ethanone (10.0 g; 0.051 m) in dry methylethyl ketone (100 ml) was added dried anhydrous sodium carbonate (27 g; 5 mol. eq) and sodium iodide (0.5 g). To the stirred suspension was then added α,α'-dibromo-p-xylene (13.5 g; 0.051 m) and the suspension gently heated at reflux for five hours. The cooled suspension was evaporated under reduced pressure, the residue dissolved in water and extracted with dichloromethane (×2). The organic extract was washed with aqueous sodium hydroxide (2N), then water, dried over magnesium sulphate, filtered, and evaporated to dryness under reduced pressure to give a yellow solid. The solid was stirred with ether (200 ml) for 1 hour and filtered to remove any disubstituted impurity. The filtrate was evaporated under reduced pressure to leave a yellow solid. The solid was chromatographed on a U30 Sorbsil solumn using dichloromethane to give a white solid; recrystallised from ethanol, m.p. 98°-99° C.

1. temperatureat reflux for five hours
2. customThe cooled suspension was evaporated under reduced pressure
3. dissolutionthe residue dissolved in water
4. extractionextracted with dichloromethane (×2)
5. extractionThe organic extract
6. washwas washed with aqueous sodium hydroxide (2N)
7. dry with materialwater, dried over magnesium sulphate
8. filtrationfiltered
9. customevaporated to dryness under reduced pressure
10. customto give a yellow solid
11. filtrationfiltered
12. customto remove any disubstituted impurity
13. customThe filtrate was evaporated under reduced pressure
14. customto leave a yellow solid
15. customThe solid was chromatographed on a U30 Sorbsil solumn
16. customto give a white solid
17. customrecrystallised from ethanol, m.p. 98°-99° C.