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

HRID 1411380

Reaction equation

HRID 1411380 reaction equation
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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

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 minutes 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 g, 61% yield).

Workup

  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

Sources & evidence

ORD record
ord-10a86b419e5c4031a6bbc43f13eba87d
Source dataset
uspto-grants-2014_12
Patent number
US08921514B2

Linked notes

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