反应详情

温度

0 °C

3-Benzyloxyaniline (2.06 g, 10.3 mmol) was dissolved in water (40 ml) and concentrated HCl (8 ml). The solution was cooled to 0° C. and solution of sodium nitrite (778 mg, 11.3 mmol) in water (10 ml) was added. After 15 min stirring at 0° C., the mixture was added to a solution of potassium ethyl xanthate (3.1 g, 20 mmol) in water (10 ml), and heated to 65° C. for 30 min. After cooling to room temperature, the reaction mixture was extracted twice with ethyl acetate. The combined organic layers were washed with 1N NaOH and water, and dried over MgSO4. The solvent was evaporated and the residue was dissolved in ethanol (50 ml). Potassium hydroxide (2 g, 40 mmol) was added and the mixture was heated to reflux for 16 h. The reaction mixture was cooled to room temperature, concentrated, and partitioned between diethylether and water. The aqueous layer was acidified to pH 1 with concentrated HCl, and then extracted twice with methylene chloride. The combined organic layers were dried over MgSO4 and the solvent was evaporated. The product was used in the next reaction step without further purification.

1. temperatureheated to 65° C. for 30 min
2. temperatureAfter cooling to room temperature
3. extractionthe reaction mixture was extracted twice with ethyl acetate
4. washThe combined organic layers were washed with 1N NaOH and water
5. dry with materialdried over MgSO4
6. customThe solvent was evaporated
7. dissolutionthe residue was dissolved in ethanol (50 ml)
8. temperaturethe mixture was heated
9. temperatureto reflux for 16 h
10. temperatureThe reaction mixture was cooled to room temperature
11. concentrationconcentrated
12. custompartitioned between diethylether and water
13. extractionextracted twice with methylene chloride
14. dry with materialThe combined organic layers were dried over MgSO4
15. customthe solvent was evaporated
16. customThe product was used in the next reaction step without further purification