Triethanolamine → 1-Ethenyl-4-nitrobenzene

HRID 1982475

Reaktionsgleichung

Reaktionsgleichung von HRID 1982475
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].N(CCO)(CCO)CCO>O>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([CH:8]=[CH2:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 7618TriethanolamineHCID 792664-Nitrophenethyl bromide

Produkt 1

HCID 74811-Ethenyl-4-nitrobenzeneAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A 500 ml 3-neck round bottom flask was fitted with a thermometer and steam distillation apparatus. The flask was charged with 12.5 g (0.054 mol) of 4-nitrophenethyl bromide, 75 ml (0.565 mol) of triethanolamine and 50 ml of water. The reaction mixture was heated to reflux and the mixture was allowed to slowly steam distill. Approximately 100 mg of hydroquinone was added to the distillate collected in order to prevent polymerization. The distillate was extracted three times with diethyl ether and the combined organic phases were washed with water, 1N hydrochloric acid, water, and a saturated sodium chloride solution in sequence. The organic phase was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure to provide 7.193 g of 4-nitrostyrene as an oil which solidified upon cooling. Additional quantities of this material were prepared by the general procedure above.

Aufarbeitung

  1. customA 500 ml 3-neck round bottom flask was fitted with a thermometer and steam distillation apparatus
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux
  4. distillationdistill
  5. additionApproximately 100 mg of hydroquinone was added to the distillate
  6. customcollected in order
  7. custompolymerization
  8. extractionThe distillate was extracted three times with diethyl ether
  9. washthe combined organic phases were washed with water, 1N hydrochloric acid, water
  10. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  11. customevaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-786fb782a4de42d6b26a5a443924864f
Quelldatensatz
uspto-grants-1986_06
Patentnummer
US04596827

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