tert-Butanol → 1,4-Bis(4-nitrophenyl)butane-1,4-dione

HRID 1470911

Reaktionsgleichung

Reaktionsgleichung von HRID 1470911
C(NCC)C.C(O)(C)(C)C.Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:14].[N+:24]([C:27]1[CH:32]=[CH:31][C:30]([C:33](=[O:35])[CH3:34])=[CH:29][CH:28]=1)([O-:26])=[O:25]>C1C=CC=CC=1.[Cl-].[Zn+2].[Cl-].O>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]([C:13](=[O:14])[CH2:12][CH2:34][C:33]([C:30]2[CH:29]=[CH:28][C:27]([N+:24]([O-:26])=[O:25])=[CH:32][CH:31]=2)=[O:35])=[CH:16][CH:17]=1)([O-:23])=[O:22]

Komponenten

8

Edukt 4

HCID 6386tert-ButanolHCID 7487p-NitroacetophenoneHCID 8021DiethylamineHCID 668402-Bromo-4'-nitroacetophenone

Produkt 1

HCID 137628911,4-Bis(4-nitrophenyl)butane-1,4-dioneAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855ZincchlorideKatalysatorHCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Anhydrous zinc(II) chloride (2.73 g, 20.00 mmol) was stirred in dry benzene (15 ml) while diethylamine (1.558 ml, 15.00 mmol) and t-butanol (1.435 ml, 15.00 mmol) were added, and the resulting mixture was stirred at room temperature for 90 min to give a cloudy solution. To this mixture was added 2-bromo-1-(4-nitrophenyl)ethanone (2.44 g, 10.00 mmol) and 1-(4-nitrophenyl)ethanone (2.477 g, 15.00 mmol), and the resulting mixture was stirred at room temperature overnight. The mixture was poured into water (50 mL) and extracted with ethyl acetate (3×50 ml). The combined organic layers were dried over Na2SO4, filtered and concentrated. The resulting residue was triturated with dichloromethane to give an orange solid that was collected by filtration and dried to give the title compound (2.0 gm, 61% yield).

Aufarbeitung

  1. additionwere added
  2. customto give a cloudy solution
  3. stirringthe resulting mixture was stirred at room temperature overnight
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was triturated with dichloromethane
  9. customto give an orange solid
  10. filtrationthat was collected by filtration
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-13b3394f990d4a35b99581f3488b3ce3
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006387B2

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