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4-Hydroxybiphenyl → 1-(4'-Phenyl-phenoxy)3,3-dimethylbutan-2-one

HRID 972749
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인쇄 미리보기

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HRID 972749 반응식
[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
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참가 물질

6

반응물 3

HCID 71034-HydroxybiphenylHCID 11430Potassium CarbonateHCID 835721-Chloropinacolone

생성물 2

HCID 835721-ChloropinacoloneHCID 230504261-(4'-Phenyl-phenoxy)3,3-dimethylbutan-2-one수율 163.5%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone
용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4a28c052a6754287ad514d3944644805
출처 데이터셋
uspto-grants-1977_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04053616

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