Iodine → 1-(But-3-en-1-yl)-4-nitrobenzene

HRID 2254989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2254989
[I-].[Na+].Br[CH:4]([CH2:16]Br)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1.II.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)C.O.CC(C)=O>[CH2:6]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)[CH2:5][CH:4]=[CH2:16]

Komponenten

8

Edukt 4

HCID 807IodineHCID 5238Sodium IodideHCID 24477Sodium ThiosulfateHCID 19739335HCID 19739335, Verbindung

Produkt 1

HCID 189934361-(But-3-en-1-yl)-4-nitrobenzeneAusbeute 89,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of 52.1 g of sodium iodide, 300 ml of acetone and 28.6 g of 1-(3,4-dibromobutyl)-4-nitrobenzene was stirred under reflux for 3.5 hours. After cooling the brown suspension was freed from solvent in vacuo and the brown residue was taken up in diethyl ether and water. The separated iodine was reduced by adding solid sodium thiosulphate. The colourless ether solutions were washed with water, dried with sodium sulphate and concentrated in vacuo. The residue (14.9 g) was distilled in a high vacuum, whereby 13.4 g of 1-(3-butenyl)-4-nitrobenzene were obtained as an almost colourless liquid; b.p. 86°-89° C./0.2 Torr.

Aufarbeitung

  1. temperatureunder reflux for 3.5 hours
  2. temperatureAfter cooling the brown suspension
  3. washThe colourless ether solutions were washed with water
  4. dry with materialdried with sodium sulphate
  5. concentrationconcentrated in vacuo
  6. distillationThe residue (14.9 g) was distilled in a high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-bf0ed1c74f014ce7ac56fc36bb6398c7
Quelldatensatz
uspto-grants-1993_08
Patentnummer
US05238602

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