反应详情

温度

-78 °C

A solution of N-phenylacridan (14.15 g, 55 mmol) in 200 mL of dry THF under inert atmosphere was cooled to −78° C. and 33.0 mL of 2.5 M n-butyllithium in hexanes (82.5 mmol) was added dropwise over 20 minutes. The solution was stirred at −78° C. for 30 minutes and then warmed to room temperature over 35 minutes. The reaction mixture was again cooled to −78° C. and 350 g of crushed dry ice was added causing a precipitate to form. The reaction was allowed to slowly warm to room temperature causing the reaction to become homogeneous. Stirring under argon was continued at room temperature. The resultant precipitate was collected by suction filtration. The solid was dissolved in 100 mL of water, which was acidified to pH 3 with 2N HCl and extracted with 4×200 mL of ethyl acetate. The combined organics were dried over sodium sulfate and concentrated to dryness to afford 8.72 g of crude product. The reaction mixture filtrate was also concentrated to dryness to afford a solid that was taken up in 300 mL of water. The aqueous solution was acidified, extracted with 3×200 mL of methylene chloride and the combined organics were dried over sodium sulfate and concentrated to afford a second crop of 3.44 g of N-phenylacridan-9-carboxylic acid (73.4%).

1. temperaturewarmed to room temperature over 35 minutes
2. temperatureThe reaction mixture was again cooled to −78° C.
3. customto form
4. temperatureto slowly warm to room temperature
5. customthe reaction
6. stirringStirring under argon
7. customwas continued at room temperature
8. filtrationThe resultant precipitate was collected by suction filtration
9. dissolutionThe solid was dissolved in 100 mL of water
10. extractionextracted with 4×200 mL of ethyl acetate
11. dry with materialThe combined organics were dried over sodium sulfate
12. concentrationconcentrated to dryness
13. customto afford 8.72 g of crude product
14. concentrationThe reaction mixture filtrate was also concentrated to dryness
15. customto afford a solid
16. extractionextracted with 3×200 mL of methylene chloride
17. dry with materialthe combined organics were dried over sodium sulfate
18. concentrationconcentrated