p-nitrophenol sodium salt → 4-(3-Butenyloxy)nitrobenzene

HRID 1112781

Reaktionsgleichung

Reaktionsgleichung von HRID 1112781
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O-:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Na+].Br[CH2:13][CH2:14][CH:15]=[CH2:16]>CN(C)C=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:16][CH2:15][CH:14]=[CH2:13])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 13214p-nitrophenol sodium saltHCID 21241Homoallyl bromide

Produkt 1

HCID 112177694-(3-Butenyloxy)nitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of sodium 4-nitrophenolate (11 grams; 56 mmole) in dimethylformamide (50 ml.) is added 4-bromo-1-butene (5 g; 37 mmole). After 2.5 hours of heating at 100° C., the reaction mixture is diluted with 400 ml. of water and extracted with light petroleum ether. The ether extracts are re-extracted with cold 5% sodium hydroxide and then washed with water and dried over magnesium sulfate. This solution is evaporated under reduced pressure and the residual oil crystallized from petroleum ether at 0° to yield 4-(4-nitrophenoxy)-1-butene.

Aufarbeitung

  1. additionthe reaction mixture is diluted with 400 ml
  2. extractionof water and extracted with light petroleum ether
  3. extractionThe ether extracts are re-extracted with cold 5% sodium hydroxide
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customThis solution is evaporated under reduced pressure
  7. customthe residual oil crystallized from petroleum ether at 0°

Quellen und Nachweise

ORD-Eintrag
ord-271b89561662433785e2307d5e40033e
Quelldatensatz
uspto-grants-1978_10
Patentnummer
US04123614

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