Реакция #93568

Уравнение реакции

(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

Растворители

water

2,2'-oxybisethanol

Условия реакции

Обработка

1. 1
   Температураwas heated gently
2. 2
   Температураat reflux temperature for 45 min
3. 3
   workup.DISTILLATIONThe low boiling material was distilled off
4. 4
   Температураthe mixture was heated
5. 5
   ДругоеThe cooled reaction mixture
6. 6
   Фильтрацияthe resulting light brown precipitate was filtered off
7. 7
   workup.DISSOLUTIONThis solid was dissolved in methylene dichloride
8. 8
   ПромывкаThe solution was washed twice with water
9. 9
   Сушкаdried (MgSO4)
10. 10
    Другоеthe solvent was removed

Методика

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.

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