반응 #93568

반응 방정식

(3-cyclopenten-1-yl)(4'-methoxy-[1,1'-biphenyl]-4-yl)-methanone

hydrazine hydrate

potassium hydroxide

hydrochloric acid

→

4-(3-cyclopenten-1-ylmethyl)-4'-hydroxy-1,1'-biphenyl

용매

water

2,2'-oxybisethanol

반응 조건

후처리

1. 1
   온도was heated gently
2. 2
   온도at reflux temperature for 45 min
3. 3
   workup.DISTILLATIONThe low boiling material was distilled off
4. 4
   온도the mixture was heated
5. 5
   기타The cooled reaction mixture
6. 6
   여과the resulting light brown precipitate was filtered off
7. 7
   workup.DISSOLUTIONThis solid was dissolved in methylene dichloride
8. 8
   세척The solution was washed twice with water
9. 9
   건조dried (MgSO4)
10. 10
    기타the solvent was removed

실험 절차

A mixture of (3-cyclopenten-1-yl)(4'-methoxy-[1,1'-biphenyl]-4-yl)-methanone (30 g), hydrazine hydrate (36 ml) and potassium hydroxide (36 g) in 2,2'-oxybisethanol (250 ml) was heated gently, at reflux temperature for 45 min. The low boiling material was distilled off and the mixture was heated under reflux, at 200° C. for 2 h. The cooled reaction mixture was poured into water, acidified with dilute hydrochloric acid and the resulting light brown precipitate was filtered off. This solid was dissolved in methylene dichloride. The solution was washed twice with water and dried (MgSO4), and the solvent was removed. Trituration of the residue with light petroleum gave 4-(3-cyclopenten-1-ylmethyl)-4'-hydroxy-1,1'-biphenyl as a buff solid (25.5 g). A small sample, recrystallised from ether-light petroleum had m.p. 138°-140° C.

출처