4,4'-Dihydroxybiphenyl → 4,4'-Bicyclohexanone

HRID 323996Notes

Reaction equation

HRID 323996 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>C1(C)C=CC=CC=1.[Pd]>[CH:8]1([CH:1]2[CH2:2][CH2:3][C:4](=[O:7])[CH2:5][CH2:6]2)[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 71124,4'-Dihydroxybiphenyl

Product 1

HCID 2648254,4'-BicyclohexanoneYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 50 g of 4,4′-biphenyldiol in 500 ml of toluene is hydrogenated at 5 bar and 125° C. in the presence of palladium on activated carbon. The reaction mixture is filtered and freed from water by azeotropic distillation. It is then treated with 29 g of pyridine sulfone and stirred at 50° C. for 1 hour. After filtration using basic alumina and removal of the solvent, 34.4 g (66% yield) of 4,4′-bicyclohexanedione remain as colourless crystals having a purity of 99.0% (GC).

Workup

  1. filtrationThe reaction mixture is filtered
  2. distillationfreed from water by azeotropic distillation
  3. additionIt is then treated with 29 g of pyridine sulfone
  4. filtrationAfter filtration

Sources & evidence

ORD record
ord-67ef23da9c564a30bafe9e80c2130e9f
Source dataset
uspto-grants-2001_04
Patent number
US06215028B1

Reaction notes

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