反应详情

温度

30 °C

To the toluene filtrate were added at room temperature 450 ml of 2N sodium hydroxide and the reaction mixture was gradually heated to reflux to minimize initial foaming. The reaction was heated at reflux for 41/2 hours. The reaction mixture was cooled to 0° to 5° C. by an ice-water bath whereupon a thick precipitate formed, consisting of the intermediate sodium 4-(3,5-di-tert-butyl-4-hydroxybenzoyloxy)-3,5-di-tert-butyl-benzoate. This compound was a white solid which did not melt at 300° C. 70 ml of concentrated aqueous hydrochloric acid was gradually added dropwise with cooling at 30° C. 150 ml of ether were added with stirring to the reaction mixture at 20° to 25° C. The aqueous phase was separated and the organic phase washed with two 100 ml portions of water. The separated organic phase was then dried over anhydrous sodium sulfate. The residue was isolated from the organic phase by evaporation of the solvent initially at about 20 mm. Hg. pressure and finally at 0.5 mm. Hg. The glassy residue was ground and then triturated with stirring at reflux with a 150 ml. portion of petroleum ether in a 3-neck flask. The slurry was then cooled to room temperature, the solid isolated by filtration and triturated once again. The white crystalline precipitate from the second trituration was dried in the vacuum oven overnight at 40° C. at 1 mm. Hg. pressure. The product was isolated as a white powder weighing 102 grams (84.5% yield). The product melted at about 301° to 306° C., the melting range depending on the heating rate.

1. temperaturethe reaction mixture was gradually heated
2. temperatureto reflux
3. temperatureThe reaction was heated
4. temperatureat reflux for 41/2 hours
5. temperatureThe reaction mixture was cooled to 0° to 5° C. by an ice-water bath whereupon a thick precipitate
6. customformed
7. customdid not melt at 300° C
8. customThe aqueous phase was separated
9. washthe organic phase washed with two 100 ml portions of water
10. dry with materialThe separated organic phase was then dried over anhydrous sodium sulfate
11. customThe residue was isolated from the organic phase by evaporation of the solvent initially at about 20 mm. Hg
12. customtriturated
13. stirringwith stirring
14. temperatureat reflux with a 150 ml
15. temperatureThe slurry was then cooled to room temperature
16. customthe solid isolated by filtration
17. customtriturated once again
18. customThe white crystalline precipitate from the second trituration was dried in the vacuum oven overnight at 40° C. at 1 mm. Hg
19. customThe product was isolated as a white powder