4,4'-Dihydroxybiphenyl → HCID 54552651, compound

HRID 1075361Notes

Reaction equation

HRID 1075361 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[K+].Br[CH2:18][CH2:19][CH:20]=[CH2:21]>CO>[CH:18]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)=[CH:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 71124,4'-DihydroxybiphenylHCID 14797Potassium HydroxideHCID 21241Homoallyl bromide

Product 1

HCID 54552651HCID 54552651, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution containing 4,4'-Dihydroxybiphenyl (5 g,26.75 mmol), KOH (1.65 g, 29.5 mmol) and methanol (50 ml) was refluxed for 2 hours. 4-Bromo-1-butene (3.975 g, 29.5 mmol) in methanol (10 ml) was added dropwise over a period of 2 hours to the refluxing reaction mixture. The refluxation was continued for 24 hours. The solvent was then removed. The product was then extracted by dichloromethane (50 ml) and dichloromethane was then removed. The resulting solid was washed with 10% potassium hydroxide solution (17 ml), filtered and recrystallized from ethanol: water (1.1 v/v) mixture. Yield 12%, m.p. 155-157° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customThe solvent was then removed
  3. extractionThe product was then extracted by dichloromethane (50 ml) and dichloromethane
  4. customwas then removed
  5. washThe resulting solid was washed with 10% potassium hydroxide solution (17 ml)
  6. filtrationfiltered
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e199c36e9faf47ca8f90fb9f96ad3827
Source dataset
uspto-grants-1999_05
Patent number
US05900145

Reaction notes

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