反应详情

Triton B (1.5 ml., 40% in MeOH) is added to a stirred solution of 1-(p-chlorophenyl)-4-phenyl-7-(m-chlorophenyl)-1,6-heptadien-3-one (22.8 g., 0.056 mole) in glyme (175 ml.), followed by addition of methyl acrylate (5.76 g., 0.067 mole) in glyme (25 ml.). After stirring for 20 hours, the solvent is removed in vacuo and water (600 ml.) and dilute hydrochloric acid (25 ml.) are added to the residue. The organic material is extracted into ether and these extracts are washed with water, saturated brine and dried (Na2SO4). After removal of the solvent the residue is heated on a steam bath with a solution of 20% sodium hydroxide (25 ml.) in methanol (300 ml.) for 48 hours. The methanol is removed in vacuo and the residue is dissolved in water (1200 ml.). Extraction with ether removes unreacted ketone. Ether is expelled from the aqueous phase by warming. The solution is cooled in an ice bath, acidified with dilute hydrochloric acid (30 ml.), and the sticky yellow solid which precipitates is collected and air-dried, yield 4.5 g., m.p. 65°-105°C. Recrystallization from benzene-petroleum ether (30°-60°C.) followed by several recrystallizations from n-butyl chloride gives material with m.p. 150°-151°C.

1. customthe solvent is removed in vacuo and water (600 ml.) and dilute hydrochloric acid (25 ml.)
2. additionare added to the residue
3. extractionThe organic material is extracted into ether
4. washthese extracts are washed with water, saturated brine
5. dry with materialdried (Na2SO4)
6. customAfter removal of the solvent the residue
7. temperatureis heated on a steam bath with a solution of 20% sodium hydroxide (25 ml.) in methanol (300 ml.) for 48 hours
8. customThe methanol is removed in vacuo
9. dissolutionthe residue is dissolved in water (1200 ml.)
10. extractionExtraction with ether
11. customremoves unreacted ketone
12. temperatureby warming
13. temperatureThe solution is cooled in an ice bath
14. customthe sticky yellow solid which precipitates
15. customis collected
16. customair-dried
17. customRecrystallization from benzene-petroleum ether (30°-60°C.)
18. customfollowed by several recrystallizations from n-butyl chloride
19. customgives material with m.p. 150°-151°C.