Diethylene Glycol → 2-Dodecylthiophene

HRID 1196801

Reaktionsgleichung

Reaktionsgleichung von HRID 1196801
[C:1]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].O.NN.C(O)CO[CH2:19][CH2:20]O.[OH-].[K+]>O>[CH2:1]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:8][CH2:1][CH2:2][CH2:3][CH2:19][CH3:20]

Komponenten

6

Edukt 4

HCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)2×HCID 5202642-Hexanoylthiophene

Produkt 1

HCID 5663472-Dodecylthiophene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

In a 5 liter-five-necked flask, 266 g (1.0 mol) of 2-hexanoylthiophene, 392.4 ml of 60% hydrazine hydrate and 3 liter of diethyleneglycol were placed and reacted for 6 hours at 195° C. with distilling-off of excessive water and hydrazine hydrate. The mixture was cooled to 50° C. and 210.6 g of KOH was added thereto, followed by heating again to react for 2.5 hours at 155° C. After the reaction, the reaction mixture was poured into 10 liter of water, extracted two times with 2 liter of isopropyl ether, followed by drying with CaCl2 and distilling-off of the solvent to obtain 229 g of a crude product. The crude product was subjected to reduced-pressure distillation in an atmosphere of nitrogen to obtain 168 g of a pure product (yield: 66.7 b.p.: 121.5° C./0.7 mmHg

Aufarbeitung

  1. temperatureby heating again
  2. customto react for 2.5 hours at 155° C
  3. customAfter the reaction
  4. extractionextracted two times with 2 liter of isopropyl ether
  5. dry with materialby drying with CaCl2 and distilling-off of the solvent
  6. customto obtain 229 g of a crude product
  7. distillationThe crude product was subjected to reduced-pressure distillation in an atmosphere of nitrogen

Quellen und Nachweise

ORD-Eintrag
ord-9c675e6536674974970239f3f52300be
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05116530

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