Réaction #93568

Équation de réaction

(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

Solvants

water

2,2'-oxybisethanol

Conditions de réaction

Traitement

1. 1
   Températurewas heated gently
2. 2
   Températureat reflux temperature for 45 min
3. 3
   workup.DISTILLATIONThe low boiling material was distilled off
4. 4
   Températurethe mixture was heated
5. 5
   AutreThe cooled reaction mixture
6. 6
   Filtrationthe resulting light brown precipitate was filtered off
7. 7
   workup.DISSOLUTIONThis solid was dissolved in methylene dichloride
8. 8
   LavageThe solution was washed twice with water
9. 9
   Séchagedried (MgSO4)
10. 10
    Autrethe solvent was removed

Mode opératoire

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.

Source