反应详情

(S)-2-Hydroxy-3-(4-hydroxy-phenyl)-propionic acid (121 g, 0.664 mol) (Wang et al. Tetrahedron Lett. 1998, 39, 5501) in absolute EtOH (2 L) was treated with potassium carbonate (184 g, 1.33 mol) and benzyl chloride 169 g, 1.34 mol). The mixture was heated at reflux overnight and concentrated to about half the volume under vacuum. Aqueous 5N NaOH (100 mL) was added, and the mixture was stirred at ambient temperature overnight and then concentrated. The residue was acidified with concentrated HCl. The yellow sold was collected by filtration and dried overnight under vacuum at 50° C. The crude product in isopropanol (1.8 L) was heated at reflux for about 30 minutes, cooled to ambient temperature, and stirred for about 16 hours. The slurry was filtered and dried under vacuum at 70° C. overnight to give the title compound as a white solid (137 g, 76%).

1. temperatureThe mixture was heated
2. temperatureat reflux overnight
3. concentrationconcentrated to about half the volume under vacuum
4. additionAqueous 5N NaOH (100 mL) was added
5. concentrationconcentrated
6. filtrationThe yellow sold was collected by filtration
7. customdried overnight under vacuum at 50° C
8. temperatureThe crude product in isopropanol (1.8 L) was heated
9. temperatureat reflux for about 30 minutes
10. temperaturecooled to ambient temperature
11. stirringstirred for about 16 hours
12. filtrationThe slurry was filtered
13. customdried under vacuum at 70° C. overnight