Hydrochloric Acid → 4'-(2-Methylbutoxy)(1,1'-biphenyl)-4-ol

HRID 648867Notes

Reaction equation

HRID 648867 reaction equation
OC1C=CC(C2C=CC(O)=CC=2)=CC=1.[OH-].[K+].[CH3:17][CH:18]([CH2:39][CH3:40])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([O:33]CC(C)CC)=[CH:29][CH:28]=2)=[CH:23][CH:22]=1.Cl>C(O)C>[CH3:17][CH:18]([CH2:39][CH3:40])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 71124,4'-DihydroxybiphenylHCID 14797Potassium HydroxideHCID 14204813Di-(2-methylbutyloxy)biphenyl

Product 1

HCID 140938154'-(2-Methylbutoxy)(1,1'-biphenyl)-4-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4,4'-dihydroxybiphenyl (500 g), ethanol (7.5 l) and KOH (302 g) was heated under reflux with stirring, followed by dropwise adding (+) brominated 2-methylbutyl (prepared from (-) 2-methylbutanol with phosphorus bromide) (530 g), reacting the mixture for 4 hours, distilling off ethanol, adding water (2 l), filtering, collecting insolubles, and treating the insolubles with toluene to remove solubles. This soluble part was recrystallized from ethanol to obtain scaly crystals having a melting point of 80.5° C.; thus it was confirmed to be di-(2-methylbutyloxy)biphenyl. On the other hand, the insoluble part was heated with hydrochloric acid with stirring, followed by cooling, collecting solids and recrystallizing from toluene and further from ethanol to obtain 4'-(2-methylbutyloxy)-4-hydroxybiphenyl having a m.p. of 137.5° C. (125 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customfor 4 hours
  4. distillationdistilling off ethanol
  5. additionadding water (2 l)
  6. filtrationfiltering
  7. customcollecting insolubles
  8. additiontreating the insolubles with toluene
  9. customto remove solubles
  10. customThis soluble part was recrystallized from ethanol
  11. customto obtain scaly crystals
  12. stirringwith stirring
  13. temperatureby cooling
  14. customcollecting solids
  15. customrecrystallizing from toluene and further from ethanol

Sources & evidence

ORD record
ord-55d6699aa2854f98b7514513f79a6d76
Source dataset
uspto-grants-1988_04
Patent number
US04737313

Reaction notes

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