反应详情

温度

31.5 °C

Triethylamine (20.2 g, 27.8 mL, 0.20 mol, 2.0 equiv) was added to a solution of 2-phenylphenol (13) (17.0 g, 0.10 mol, 1.0 equiv) in THF (200 mL) followed by solid magnesium chloride (14.3 g, 0.15 mol, 1.5 equiv). The reaction temperature increased from 23 to 40° C. over ˜10 min. The reaction mixture was stirred an additional 10 min during which time a light tan suspension formed. Paraformaldehyde (15.0 g, 0.5 mol, 5.0 equiv) was added and the mixture heated to reflux with formation of a yellow suspension. The mixture was refluxed for 2.5 hr, allowed to slowly cool to room temperature and stirred overnight. The mixture was diluted with EtOAc and 1N HCl (300 mL) with mild cooling to keep the reaction temperature at <25° C. The mixture was transferred to a separatory funnel and shaken with an additional 1N HCl (200 mL). The organic phase was washed with brine (300 mL), dried over Na2SO4, filtered and the solution concentrated under reduced pressure giving a yellow oil that partially crystallized. The oily crystalline material was pumped on high vacuum for 1 hr to give 20.6 g (104%) of crude 14 that was used without further purification.

1. customformed
2. temperaturethe mixture heated
3. temperatureto reflux with formation of a yellow suspension
4. temperatureThe mixture was refluxed for 2.5 hr
5. temperatureto slowly cool to room temperature
6. stirringstirred overnight
7. temperaturewith mild cooling
8. customat <25° C
9. customThe mixture was transferred to a separatory funnel
10. washThe organic phase was washed with brine (300 mL)
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. concentrationthe solution concentrated under reduced pressure
14. customgiving a yellow oil
15. customthat partially crystallized
16. waitThe oily crystalline material was pumped on high vacuum for 1 hr
17. customto give 20.6 g (104%) of crude 14 that
18. customwas used without further purification