反应详情

1 g of 2,4-Dichlorophenol was dissolved in 15 ml of N,N-dimethylformamide, and 0.27 g of 60% sodium hydride was added thereto under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. 1.1 ml of Ethyl α-bromopropionate was added to the mixture, and stirring was continued at room temperature for another 1 hour. To the reaction solution was added aqueous ammonium chloride, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The residue was subjected to silica gel column chromatography, and the fraction eluted with 50:1 n-hexane:ethyl acetate was evaporated and the residue was dissolved in ethanol. To this solution was added 6.5 ml of 5N sodium hydroxide. It was then refluxed for 1 hour. The reaction solution was cooled, and water was added thereto. Then, the mixture was acidified with dilute hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated, to give 1.5 g of the title compound.

1. temperatureunder ice-cooling
2. stirringstirring
3. waitwas continued at room temperature for another 1 hour
4. extractionthe mixture was extracted with ethyl acetate
5. washThe organic layer was washed with brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customthe solvent was evaporated
8. washthe fraction eluted with 50:1 n-hexane
9. customethyl acetate was evaporated
10. dissolutionthe residue was dissolved in ethanol
11. additionTo this solution was added 6.5 ml of 5N sodium hydroxide
12. temperatureIt was then refluxed for 1 hour
13. temperatureThe reaction solution was cooled
14. additionwater was added
15. extractionextracted with ethyl acetate
16. washThe organic layer was washed with brine
17. dry with materialdried over anhydrous magnesium sulfate
18. customthe solvent was evaporated