反应详情

温度

-10 °C

110 g of 2-nitro-4-n-butyl-aniline (prepared as described in Example 1) were suspended in 400 ml of toluolated ethanol and 300 ml of concentrated hydrochloric acid and diazotized at 5°-10° C. with 34 g of sodium nitrite dissolved in 100 ml of water, following the same procedure as described for Example 1. The clear diazonium solution was added very slowly to a cold solution obtained by dissolving 74 g of 2-sec.-butyl-4-tert.-butylphenol in 200 ml of ethanol and 150 ml of sodium hydroxide 30% aqueous solution. The mixture obtained was stirred for 2 hours keeping the temperature at 0° C. The solution was then cooled at -10° C. and the gummy solid obtained, 2-(2'-hydroxy-3'-sec.-butyl-5'-tert.-butyl-phenyl)-3-nitro5-n-butyl-azobenzene, was filtered on a Buchner funnel and washed with cold water. The product was dissolved in 300 ml of ethanol and 20 ml of sodium hydroxide 30% water solution and 130 g of zinc powder were slowly added to the well-stirred solution to keep the temperature below 30° C. At the end of the addition the reaction mixture was heated to reflux under stirring for two hours, cooled to 30° C. and filtered. The filtered solution was poured onto 1,000 ml of ice and water and acidified with 500 ml of concentrated hydrochloric acid, thus obtaining the separation of the product as oil. This oil was extracted with ethyl ether, the ethereal extracts dried over anhydrous sodium sulfate overnight. After filtration and removal of the solvent, the oil was purified by distillation under vacuum, collecting the fraction boiling at 218°-219° C./0.5 mm Hg. The structure has been confirmed by N.M.R. and the acidimetric title (--OH) of the compound resulting in 97% Spectral properties: λmax =342 nm.; εmolar =1.8.104.

1. customobtained
2. customThe mixture obtained
3. customat 0° C
4. customthe gummy solid obtained
5. filtration2-(2'-hydroxy-3'-sec.-butyl-5'-tert.-butyl-phenyl)-3-nitro5-n-butyl-azobenzene, was filtered on a Buchner funnel
6. washwashed with cold water
7. dissolutionThe product was dissolved in 300 ml of ethanol
8. addition20 ml of sodium hydroxide 30% water solution and 130 g of zinc powder were slowly added to the well-stirred solution
9. customthe temperature below 30° C
10. additionAt the end of the addition the reaction mixture
11. temperaturewas heated
12. temperatureto reflux
13. stirringunder stirring for two hours
14. temperaturecooled to 30° C.
15. filtrationfiltered
16. additionThe filtered solution was poured onto 1,000 ml of ice and water
17. customthus obtaining
18. customthe separation of the product as oil
19. extractionThis oil was extracted with ethyl ether
20. dry with materialthe ethereal extracts dried over anhydrous sodium sulfate overnight
21. filtrationAfter filtration and removal of the solvent
22. distillationthe oil was purified by distillation under vacuum
23. customcollecting the fraction boiling at 218°-219° C./0.5 mm Hg
24. customand the acidimetric title (--OH) of the compound resulting in 97% Spectral properties