反应详情

温度

50 °C

N-Benzylethanolamine (459 g) is mixed with 1,2-epoxy-3-methoxypropane (422 g) and the mixture is stirred at 50° C. for 16 hours and thereafter the excess 1,2-epoxy-3-methoxypropane is distilled off under reduced pressure. The residue is dissolved in 1,4-dioxane (3 liters) and thereto are added powdery potassium hydroxide (692.5 g) and tris(3,6-dioxaheptyl)amine (11.4 g). To the mixture is added dropwise with stirring a solution of p-toluenesulfonyl chloride (809.4 g) in 1,4-dioxane (2 liters) over a period of 1.5 hour, during which the temperature of the reaction mixture raises and the solvent is refluxed. After the dropwise addition, the mixture is stirred for 2 hours, and the undissolved materials are filtered off and washed with ethyl acetate. The filtrate and the washing liquid are combined and distilled under reduced pressure to remove the solvent. To the residue are added water (600 ml) and conc. hydrochloric acid (300 ml) to make acidic. The aqueous layer is washed with ethyl acetate, made strongly basic by adding sodium hydroxide (160 g) under ice cooling and extracted with ethyl acetate. The ethyl acetate layer is washed with saturated saline solution, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The obtained residue is distilled under reduced pressure to give the title compound (391.3 g) as colorless liquid.

1. distillationthe excess 1,2-epoxy-3-methoxypropane is distilled off under reduced pressure
2. dissolutionThe residue is dissolved in 1,4-dioxane (3 liters)
3. additionare added powdery potassium hydroxide (692.5 g) and tris(3,6-dioxaheptyl)amine (11.4 g)
4. additionTo the mixture is added dropwise
5. stirringwith stirring a solution of p-toluenesulfonyl chloride (809.4 g) in 1,4-dioxane (2 liters) over a period of 1.5 hour
6. temperatureduring which the temperature of the reaction mixture raises
7. temperaturethe solvent is refluxed
8. additionAfter the dropwise addition
9. stirringthe mixture is stirred for 2 hours
10. filtrationthe undissolved materials are filtered off
11. washwashed with ethyl acetate
12. distillationdistilled under reduced pressure
13. customto remove the solvent
14. additionTo the residue are added water (600 ml) and conc. hydrochloric acid (300 ml)
15. washThe aqueous layer is washed with ethyl acetate
16. additionby adding sodium hydroxide (160 g) under ice cooling
17. extractionextracted with ethyl acetate
18. washThe ethyl acetate layer is washed with saturated saline solution
19. dry with materialdried over anhydrous magnesium sulfate
20. distillationdistilled under reduced pressure
21. customto remove the solvent
22. distillationThe obtained residue is distilled under reduced pressure