4-Hydroxybiphenyl → 1-([1,1′-Biphenyl]-4-yloxy)-3,3-dimethyl-2-butanone

HRID 972749Notes

Reaction equation

HRID 972749 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:20][C:21]([C:24]([CH2:26][Cl:27])=[O:25])([CH3:23])[CH3:22]>C(C(C)=O)C>[CH3:20][C:21]([C:24]([CH2:26][Cl:27])=[O:25])([CH3:23])[CH3:22].[C:8]1([C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:26][C:24](=[O:25])[C:21]([CH3:23])([CH3:22])[CH3:20])=[CH:7][CH:6]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 71034-HydroxybiphenylHCID 11430Potassium CarbonateHCID 835721-Chloropinacolone

Product 2

HCID 835721-ChloropinacoloneHCID 230504261-([1,1′-Biphenyl]-4-yloxy)-3,3-dimethyl-2-butanoneYield 163.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

510 g (3 moles) of 4-hydroxybiphenyl were dissolved in 3 l of methyl ethyl ketone. 390 g of ground potassium carbonate were added and the mixture was heated to 80° C. 405 g (3 moles) of α-chloropinacoline were added dropwise over the course of 2 hours and the mixture was then stirred for a further 15 hours at 80° C. After cooling, it was filtered and the filter residue was rinsed with methyl ethyl ketone. The resulting filtrate was concentrated to dryness in vacuo by distilling off the solvent. The residue was taken up in methylene chloride and the solution was washed with 10% strength sodium hydroxide solution and twice with water, dried over sodium sulfate and concentrated in vacuo by distilling off the solvent. The residue was distilled, using a condenser cooled with hot water (50° C.), to avoid crystallization. After a small amount of first runnings of chloropinacoline at 40° C./0.4 mm Hg, 658 g (82% of theory) of 1-(4'-phenyl-phenoxy)3,3-dimethylbutan-2-one were obtained at 170° to 180° C./0.4 mm Hg.

Workup

  1. temperatureAfter cooling
  2. filtrationit was filtered
  3. washthe filter residue was rinsed with methyl ethyl ketone
  4. concentrationThe resulting filtrate was concentrated to dryness in vacuo
  5. distillationby distilling off the solvent
  6. washthe solution was washed with 10% strength sodium hydroxide solution and twice with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. distillationby distilling off the solvent
  10. distillationThe residue was distilled
  11. temperaturecooled with hot water (50° C.)
  12. customcrystallization

Sources & evidence

ORD record
ord-4a28c052a6754287ad514d3944644805
Source dataset
uspto-grants-1977_10
Patent number
US04053616

Reaction notes

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