4,4'-Dihydroxybiphenyl → HCID 22168361, compound

HRID 1031759Notes

Reaction equation

HRID 1031759 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]Br)[CH:2]=[CH2:3].[C:14]1([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.[OH-].[K+]>CO>[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:20][C:17]1[CH:16]=[CH:15][C:14]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)=[CH:19][CH:18]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 71124,4'-DihydroxybiphenylHCID 14797Potassium HydroxideHCID 19797894HCID 19797894, compound

Product 1

HCID 22168361HCID 22168361, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7.0 g of 8-bromooctyl allyl ether, 11.0 g of biphenyl-4,4'-diol, and 8.0 g of potassium hydroxide was refluxed in methanol for 20 hours. After distilling methanol out under reduced pressure, acetone was added to the resulting solution, and hydrochloric acid was then added dropwise to the solution. After removing the insoluble matters away by filtration, the solvent was distilled out under reduced pressure. The residue was recrystallized from ethanol to obtain 7.2 g of the objective phenol compound. (Yield: 72%).

Workup

  1. distillationAfter distilling methanol out under reduced pressure, acetone
  2. additionwas added to the resulting solution, and hydrochloric acid
  3. additionwas then added dropwise to the solution
  4. customAfter removing the insoluble matters
  5. filtrationaway by filtration
  6. distillationthe solvent was distilled out under reduced pressure
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-823c62f2ad604536baa96fa3a7e3c7c1
Source dataset
uspto-grants-1990_09
Patent number
US04954600

Reaction notes

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