反应详情

温度

120 °C

A 500 mL three-neck flask was charged with 4-hydroxybenzophenone (80.00 g; 0.4036 mol), 1-bromo-3-chloropropane (76.25 g; 0.4843 mol) and 4-methyl-2-pentanone (330 mL). Anhydrous potassium carbonate (61.36 g; 0.4440 mol) was added and the reaction mixture was stirred at reflux (120° C.) for 4 h. HPLC analysis shows that the reaction mixture contains 90.0% 4-(3-chloropropoxy)benzophenone; 7.0% 1,3-bis(4-benzoylphenoxy)propane and 0.8% 4-hydroxybenzophenone. The reaction mixture was filtered hot and the inorganic solids were washed with 4-methyl-2-pentanone (100 mL). The filtrate was charged into a mixture of diethanolamine (148.5 g; 1.412 mol), sodium iodide (6.05 g; 0.0404 mol) and 4-methyl-2-pentanone (150 mL). The reaction mixture heated to reflux (122° C.) for 24 h. The reaction mixture was cooled to room temperature and extracted with water (500 mL). The organic phase was extracted with 1 M HCl (500 mL) at 70° C. to prevent crystallisation of the 1,3-bis(4-benzoylphenoxy)propane byproduct. The aqueous phase was separated, cooled to room temperature and taken to pH 12 with 50% aqueous NaOH. The resulting emulsion was extracted with 4-methyl-2-pentanone (3×200 mL). The organic phase was separated, dried (MgSO4), filtered and the solvent removed in vacuo. This provides 4-{3-[bis(2-hydroxyethyl)amino]propoxy}benzophenone (123.2 g; 89% yield over 3 steps).

1. filtrationThe reaction mixture was filtered hot
2. washthe inorganic solids were washed with 4-methyl-2-pentanone (100 mL)
3. temperatureThe reaction mixture heated
4. temperatureto reflux (122° C.) for 24 h
5. temperatureThe reaction mixture was cooled to room temperature
6. extractionextracted with water (500 mL)
7. extractionThe organic phase was extracted with 1 M HCl (500 mL) at 70° C.
8. customcrystallisation of the 1,3-bis(4-benzoylphenoxy)propane byproduct
9. customThe aqueous phase was separated
10. temperaturecooled to room temperature
11. extractionThe resulting emulsion was extracted with 4-methyl-2-pentanone (3×200 mL)
12. customThe organic phase was separated
13. dry with materialdried (MgSO4)
14. filtrationfiltered
15. customthe solvent removed in vacuo