反应详情

22 g of p-phenylphenol was dissolved in 95% ethanol; a solution of 40 g of sodium hydroxide in 80 ml of water was rapidly added. The resulting solution was heated to 75°-80° C. and 20 ml of chloroform was added over a one-hour period, the mixture being gently refluxed. The mixture then was stirred for three hours, cooled and the ethanol and excess chloroform were evaporated under reduced pressure. The resulting residue was cooled and poured into cold water. The resulting mixture was acidified by slow addition of hydrochloric acid and extracted with ether. The solvent was evaporated from the extract under reduced pressure, the residue was poured in twice its volume of saturated sodium metabisulfite solution and the mixture was shaken vigorously for forty-five minutes. The resulting semisolid bisulfite addition compound was allowed to stand for one hour, filtered in the dark and washed with small portions of ethanol and ether to remove the phenol. The bisulfite addition compound with decomposed with dilute sulfuric acid, the mixture being warmed on a water-bath for thirty minutes. The cooled mixture was extracted with ether, dried (Na2SO4), and the solvent was evaporated under reduced pressure. The residue was treated with activated charcoal and recrystallized from ethanol/water to give 5-phenylsalicylaldehyde (1A). as yellow crystals, mp: 98°-99° C.

1. temperatureThe resulting solution was heated to 75°-80° C.
2. temperaturethe mixture being gently refluxed
3. temperaturecooled
4. customthe ethanol and excess chloroform were evaporated under reduced pressure
5. temperatureThe resulting residue was cooled
6. additionpoured into cold water
7. additionThe resulting mixture was acidified by slow addition of hydrochloric acid
8. extractionextracted with ether
9. customThe solvent was evaporated from the
10. extractionextract under reduced pressure
11. additionthe residue was poured in twice its volume of saturated sodium metabisulfite solution
12. stirringthe mixture was shaken vigorously for forty-five minutes
13. additionThe resulting semisolid bisulfite addition compound
14. waitto stand for one hour
15. filtrationfiltered in the dark
16. washwashed with small portions of ethanol and ether
17. customto remove the phenol
18. additionThe bisulfite addition compound with decomposed with dilute sulfuric acid
19. temperaturethe mixture being warmed on a water-bath for thirty minutes
20. extractionThe cooled mixture was extracted with ether
21. dry with materialdried (Na2SO4)
22. customthe solvent was evaporated under reduced pressure
23. additionThe residue was treated with activated charcoal
24. customrecrystallized from ethanol/water