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Acetic Acid → 5,6-Methylenedioxy-2-nitro-3-phenylbenzofuran

HRID 46625
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 46625
Br[C:2]1[O:3][C:4]2[CH:16]=[C:15]3[O:17][CH2:18][O:19][C:14]3=[CH:13][C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(O)(=O)C.C1CCC(C(O)=O)CC=1.[N+:33]([O-:38])([N+]([O-])=O)=[O:34]>O>[CH2:18]1[O:17][C:15]2=[CH:16][C:4]3[O:3][C:2]([N+:33]([O-:38])=[O:34])=[C:6]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:5]=3[CH:13]=[C:14]2[O:19]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic Acid2×HCID 209033-Cyclohexene-1-carboxylic acidHCID 25352Nitrogen oxide (N2O4)HCID 544242002-Bromo-5,6-methylenedioxy-3-phenylbenzofuran

Produkt 1

HCID 541688035,6-Methylenedioxy-2-nitro-3-phenylbenzofuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Versuchsvorschrift

To a solution of 5.2 g. (0.016 mole) of 2-bromo-5,6-methylenedioxy-3-phenylbenzofuran in 225 ml. of acetic acid is added with stirring 5.0 g. (0.024 mole) of cyclohexene-4-carboxylic acid, then 2.2 g. (0.024 mole) of dinitrogen tetraoxide in 25 ml. of acetic acid. After about one hour the mixture is poured into cold water, and the yellow product is collected and washed with water. The product is dissolved in dichloromethane, and the solution is washed with cold 5 percent sodium hydroxide solution, water and saturated sodium chloride solution, then dried. The solution is concentrated to dryness to provide a yellow residue which is recrystallized from a benzene-hexane mixture, then from an isopropanol-benzene mixture to provide yellow needles of 5,6-methylenedioxy-2-nitro-3-phenylbenzofuran, m.p. 180°-183° C.

Aufarbeitung

  1. customthe yellow product is collected
  2. washwashed with water
  3. dissolutionThe product is dissolved in dichloromethane
  4. washthe solution is washed with cold 5 percent sodium hydroxide solution, water and saturated sodium chloride solution
  5. customdried
  6. concentrationThe solution is concentrated to dryness
  7. customto provide a yellow residue which
  8. customis recrystallized from a benzene-hexane mixture

Quellen und Nachweise

ORD-Eintrag
ord-a38d89104c9f443cab73e1460278556b
Quelldatensatz
uspto-grants-1979_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04174403

Notizen zur Reaktion

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