反应详情

温度

70 °C

1,2,2,6,6-Pentamethyl-piperidin-4-one (8.64 g, 50.00 mmol) and phenol (4.98 g, 53.00 mmol) were melted together at 60° C. in a 100 mL round bottomed flask after which 13.5 mL of concentrated hydrochloric acid was added dropwise. The yellow solution was stirred at 70° C. for 24 hours. The mixture was poured into a beaker containing ice. Ammonium hydroxide was added carefully while stirring until the pH reached 7˜8. The mixture was extracted with EtOAc five times. The organic phases were combined, dried (Na2SO4) and concentrated. The residue was purified by chromatography on a silica gel column, eluting with 7N NH3 in methanol/dichloromethane to give 4-(1,2,2,6,6-pentamethyl-1,2,3,6-tetrahydropyridin-4-yl)-phenol (4.11 g, 34%).

1. additionThe mixture was poured into a beaker
2. additioncontaining ice
3. stirringwhile stirring until the pH
4. extractionThe mixture was extracted with EtOAc five times
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated
7. customThe residue was purified by chromatography on a silica gel column
8. washeluting with 7N NH3 in methanol/dichloromethane