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

HRID 1470911

反応式

HRID 1470911 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 241Benzene溶媒HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-13b3394f990d4a35b99581f3488b3ce3
出典データセット
uspto-grants-2015_04
特許番号
US09006387B2

関連ノート

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