تفاعل #93568

معادلة التفاعل

(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

المذيبات

water

2,2'-oxybisethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated gently
2. 2
   درجة الحرارةat reflux temperature for 45 min
3. 3
   workup.DISTILLATIONThe low boiling material was distilled off
4. 4
   درجة الحرارةthe mixture was heated
5. 5
   أخرىThe cooled reaction mixture
6. 6
   ترشيحthe resulting light brown precipitate was filtered off
7. 7
   workup.DISSOLUTIONThis solid was dissolved in methylene dichloride
8. 8
   غسيلThe solution was washed twice with water
9. 9
   تجفيفdried (MgSO4)
10. 10
    أخرىthe solvent was removed

الإجراء التجريبي

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.

المصدر