Hydrochloric Acid → 4-(3-Cyclopenten-1-ylmethyl)-4'-hydroxy-1,1'-biphenyl

HRID 65290Notes

Reaction equation

HRID 65290 reaction equation
[CH:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)=O)[CH2:5][CH:4]=[CH:3][CH2:2]1.O.NN.[OH-].[K+].Cl>O(CCO)CCO.O>[CH:1]1([CH2:6][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)[CH2:2][CH:3]=[CH:4][CH2:5]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 20234281(3-Cyclopenten-1-yl)(4'-methoxy-[1,1'-biphenyl]-4-yl)-methanone

Product 1

HCID 202343454-(3-Cyclopenten-1-ylmethyl)-4'-hydroxy-1,1'-biphenyl

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8117Diethylene GlycolSolvent

Conditions

Temperature
200 °C

Procedure

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.

Workup

  1. temperaturewas heated gently
  2. temperatureat reflux temperature for 45 min
  3. distillationThe low boiling material was distilled off
  4. temperaturethe mixture was heated
  5. customThe cooled reaction mixture
  6. filtrationthe resulting light brown precipitate was filtered off
  7. dissolutionThis solid was dissolved in methylene dichloride
  8. washThe solution was washed twice with water
  9. dry with materialdried (MgSO4)
  10. customthe solvent was removed

Sources & evidence

ORD record
ord-082980ae059a41dbbd3375aa8ea50ec3
Source dataset
uspto-grants-1986_09
Patent number
US04613619

Reaction notes

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