Nitric Acid → 5-Methyl-2-nitro-3-phenylbenzofuran

HRID 1391318Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1391318
Br[C:2]1[O:3][C:4]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1CCC(C(O)=O)CC=1.[N:27]([O-:29])=[O:28].[Na+].[N+]([O-])(O)=O>C(O)(=O)C>[CH3:17][C:14]1[CH:15]=[CH:16][C:4]2[O:3][C:2]([N+:27]([O-:29])=[O:28])=[C:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:5]=2[CH:13]=1

Komponenten

6

Edukt 4

HCID 944Nitric AcidHCID 209033-Cyclohexene-1-carboxylic acidHCID 213309222-Bromo-5-methyl-3-phenylbenzofuranHCID 23668193Sodium Nitrite

Produkt 1

HCID 203338115-Methyl-2-nitro-3-phenylbenzofuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 25 g (0.0875 mole) of 2-bromo-5-methyl-3-phenylbenzofuran and 16.5 g of cyclohexene-4-carboxylic acid in 150 ml of acetic acid is added 17.5 g of sodium nitrite, then 17.5 ml of nitric acid is added dropwise with stirring. The mixture is stirred at about 25° C. for about three hours, then poured onto ice. The mixture is then extracted with diethyl ether. The ether solution is washed with 10% sodium bicarbonate solution, saturated sodium carbonate solution and dried. The dried solution is evaporated under vacuum to provide a yellow residue. The residue is recrystallized from carbon tetrachloride, then cyclohexane to provide yellow crystals of 5-methyl-2-nitro-3-phenylbenzofuran, m.p. 144.5°-146° C.

Aufarbeitung

  1. stirringThe mixture is stirred at about 25° C. for about three hours
  2. additionpoured onto ice
  3. extractionThe mixture is then extracted with diethyl ether
  4. washThe ether solution is washed with 10% sodium bicarbonate solution, saturated sodium carbonate solution
  5. customdried
  6. customThe dried solution is evaporated under vacuum
  7. customto provide a yellow residue
  8. customThe residue is recrystallized from carbon tetrachloride

Quellen und Nachweise

ORD-Eintrag
ord-521b43630ce6493c99bdb2ac140bdb98
Quelldatensatz
uspto-grants-1979_02
Patentnummer
US04141990

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