Reaktion #93568

Reaktionsgleichung

(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

Lösungsmittel

water

2,2'-oxybisethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated gently
2. 2
   Temperaturat reflux temperature for 45 min
3. 3
   workup.DISTILLATIONThe low boiling material was distilled off
4. 4
   Temperaturthe mixture was heated
5. 5
   SonstigeThe 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
   WaschenThe solution was washed twice with water
9. 9
   Trocknendried (MgSO4)
10. 10
    Sonstigethe solvent was removed

Vorschrift

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.

Quelle