Water → 4,4'-Dihydroxybiphenyl

HRID 1249639Notes

Reaction equation

HRID 1249639 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][C:14](S([O-])(=O)=O)=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4](S([O-])(=O)=O)=[CH:3][CH:2]=1.[K+].[K+].[OH-:23].[K+].[OH2:25]>>[C:4]1([OH:25])[CH:5]=[CH:6][C:1]([C:11]2[CH:16]=[CH:15][C:14]([OH:23])=[CH:13][CH:12]=2)=[CH:2][CH:3]=1

Participants

4

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 6096960[1,1'-Biphenyl]-4,4'-disulfonic acid, potassium salt (1:2)

Product 1

HCID 71124,4'-DihydroxybiphenylYield 95.6%

Conditions

Temperature
310 °C

Procedure

Dipotassium 4,4'-biphenyldisulfonate (195 g) was added to 448 g of a 50% aqueous solution of potassium hydroxide, and the mixture was stirred. Then, 1680 g of a hydrogenated triphenyl mixture was mixed. The mixture was heated to 310° C. in an atmosphere of nitrogen, and with stirring, it was dehydrated. Thereafter, the mixture was stirred at 310° C. for 3 hours. After cooling, 1 liter of water was added to the reaction mixture to separate the triphenyl hydrogenated layer. The water layer was decolorized with activated carbon, and precipitated with dilute sulfuric acid to give 88.9 g (yield 95.6%) of 4,4'-biphenol.

Workup

  1. stirringwith stirring
  2. stirringThereafter, the mixture was stirred at 310° C. for 3 hours
  3. temperatureAfter cooling
  4. customto separate the triphenyl hydrogenated layer
  5. customprecipitated with dilute sulfuric acid

Sources & evidence

ORD record
ord-e031ac6d1739434e8c25b55b6a29468c
Source dataset
uspto-grants-1986_12
Patent number
US04633024

Reaction notes

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