Potassium Hydroxide → 4-Pentylbiphenyl

HRID 328308Notes

Reaction equation

HRID 328308 reaction equation
[C:1]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)(=O)[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].[K+].O.NN>C(O)COCCO>[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 30848821-Pentanone, 1-[1,1'-biphenyl]-4-yl-

Product 1

HCID 815464-PentylbiphenylYield 70%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
50 °C

Procedure

Thousand gram of 4-n-pentanoylbiphenyl, 2 l of diethylene glycol and 564 g of potassium hydroxide were introduced into a 5 l three neck flask and warmed with stirring to give a uniform solution at about 80° C, which was then cooled to about 50° C, followed by adding 738 ml of hydrazine hydrate, heating with stirring, distilling off low boiling fractions (mainly water) until the temperature of the reaction mixture reached 185° C, heating under reflux at 185°-190° C for 4 hours, cooling to room temperature, adding 1.5 l of water and 400 ml of hexane, stirring, washing hexane layer with aqueous solution of sodium chloride, and distilling, to give 659 g of 4-n-pentylbiphenyl (b.p. 166°-167°/6 mmHg) (Yield 70%).

Workup

  1. temperaturewarmed
  2. customto give a uniform solution at about 80° C
  3. temperatureheating
  4. stirringwith stirring
  5. distillationdistilling off low boiling fractions (mainly water) until the temperature of the reaction mixture
  6. customreached 185° C
  7. temperatureheating
  8. temperatureunder reflux at 185°-190° C for 4 hours
  9. temperaturecooling to room temperature
  10. additionadding 1.5 l of water and 400 ml of hexane
  11. stirringstirring
  12. washwashing hexane layer with aqueous solution of sodium chloride
  13. distillationdistilling

Sources & evidence

ORD record
ord-a2b4ce62374c4ef5991517acd6ea60bb
Source dataset
uspto-grants-1977_04
Patent number
US04017416

Reaction notes

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