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Hydrogen Peroxide → 2-(2',4'-Dichloro-4-ethylbiphenyl-3-yl)-4,4,6,6-tetramethyl-1,5-dioxaspiro[2.4]heptan-7-one

HRID 1193244
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1193244
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[C:11]([CH:17]=[C:18]2[C:22]([CH3:24])([CH3:23])[O:21][C:20]([CH3:26])([CH3:25])[C:19]2=[O:27])[CH:10]=1.[OH:28]O.[OH-].[Li+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[C:11]([CH:17]2[C:18]3([C:19](=[O:27])[C:20]([CH3:26])([CH3:25])[O:21][C:22]3([CH3:24])[CH3:23])[O:28]2)[CH:10]=1
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Komponenten

5

Edukt 3

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 668237254-[1-(2',4'-Dichloro-4-ethylbiphenyl-3-yl)-methylidene]-2,2,5,5-tetramethyldihydrofuran-3-one

Produkt 1

HCID 866636752-(2',4'-Dichloro-4-ethylbiphenyl-3-yl)-4,4,6,6-tetramethyl-1,5-dioxaspiro[2.4]heptan-7-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887Methanol
Lösungsmittel

Versuchsvorschrift

To a solution of 4-[1-(2′,4′-dichloro-4-ethylbiphenyl-3-yl)-methylidene]-2,2,5,5-tetramethyldihydrofuran-3-one (2.04 g, 0.0051 mol) in methanol (24 ml) at 55° C. is added hydrogen peroxide solution (0.43 ml, 0.0076 mmol, 50% wt solution), followed immediately by aqueous lithium hydroxide (0.25 ml, 0.0005 mol). The reaction mixture is heated at this temperature for 30 minutes, then is rapidly cooled to room temperature and quenched with saturated sodium thiosulphate. The crude product is extracted with diethyl ether (×3), washed with saturated sodium bicarbonate, then dried over magnesium sulfate. The residue is purified by flash column chromatography (5% ethyl acetate in isohexane to 25% ethyl acetate in isohexane) to afford 2-(2′,4′-dichloro-4-ethylbiphenyl-3-yl)-4,4,6,6-tetramethyl-1,5-dioxaspiro[2.4]heptan-7-one as a yellow gum.

Aufarbeitung

  1. temperatureThe reaction mixture is heated at this temperature for 30 minutes
  2. customquenched with saturated sodium thiosulphate
  3. extractionThe crude product is extracted with diethyl ether (×3)
  4. washwashed with saturated sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. customThe residue is purified by flash column chromatography (5% ethyl acetate in isohexane to 25% ethyl acetate in isohexane)

Quellen und Nachweise

ORD-Eintrag
ord-e3aee90f19664db2b6866256c8d3c0c2
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08680299B2

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