4,4'-Dihydroxybiphenyl → (1,1'-Bicyclohexyl)-4,4'-diol

HRID 1165616Notes

Reaction equation

HRID 1165616 reaction equation
[C:1]1([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH:6]=[CH:5][C:4]([OH:7])=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[H][H]>C(O)(C)C.O1CCCC1.[Pd]>[CH2:6]1[CH:1]([CH:8]2[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]2)[CH2:2][CH2:3][CH:4]([OH:7])[CH2:5]1

Participants

7

Reactant 3

HCID 71124,4'-DihydroxybiphenylHCID 10340Sodium CarbonateHCID 178418361HCID 178418361, compound

Product 1

HCID 88608(1,1'-Bicyclohexyl)-4,4'-diol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 1 l of isopropanol was dissolved 100 g (0.54 mol) of biphenyl-4,4'-diol, and 5 g of anhydrous sodium carbonate and 5 g of 5% palladium-on-carbon were added to the solution. The mixture was subjected to reduction reaction in an autoclave at 100° C. and at a hydrogen pressure of 5 kg/cm2 for 25 to 30 hours. After completion of the reaction, the reaction mixture was filtered, and the isopropanol was removed from the filtrate by distillation under reduced pressure to recover a part of dicyclohexyl-4,4'-diol. The crystals obtained as a filter cake were dissolved in 500 ml of tetrahydrofuran while hot and filtered. The tetrahydrofuran was removed from the filtrate by distillation under reduced pressure to obtain dicyclohexyl-4,4'-diol. Both crystals were combined, suspended in 1 l of n-hexane while hot, and allowed to stand at 5° to 6° C. for 1 hour. The precipitated crystals were collected by filtration and dried under reduced pressure to obtain 93 g (0.47 mol) of a compound of formula: ##STR28## Melting Point: 179°-181° C.

Workup

  1. additionwere added to the solution
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered
  4. customthe isopropanol was removed from the filtrate by distillation under reduced pressure
  5. customto recover a part of dicyclohexyl-4,4'-diol
  6. customThe crystals obtained as a filter cake
  7. filtrationfiltered
  8. customThe tetrahydrofuran was removed from the filtrate by distillation under reduced pressure

Sources & evidence

ORD record
ord-4b162e6111c247de951ba3215fccf4b4
Source dataset
uspto-grants-1990_03
Patent number
US04910350

Reaction notes

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