Acetone → Diethyl isophthalate

HRID 1783276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1783276
BrCCCCCCOC1C=CC(C2C=CC(C#N)=CC=2)=CC=1.O[C:24]1[CH:25]=[C:26]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:27]=[C:28]([CH:34]=1)[C:29]([O:31][CH2:32][CH3:33])=[O:30].CC(C)=O>O>[C:29]([O:31][CH2:32][CH3:33])(=[O:30])[C:28]1[CH:34]=[CH:24][CH:25]=[C:26]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:27]=1

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 6064565-Hydroxy-isophthalic acid diethyl esterHCID 23432392HCID 23432392, Verbindung

Produkt 1

HCID 12491Diethyl isophthalateAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

0.08 mol (28.8 g) of 4-(6-bromohexyloxy)-4′-cyanobiphenyl, 0.08 mol (16.6 g) of diethyl 5-hydroxyisophthalate, 0.12 mol (19.2 g) of potassium carbonate anhydride and 400 ml of acetone were placed in a 1 l three-neck flask and the mixture was reacted under reflux for 24 hours by using a water bath. After the reaction solution was allowed to cool, it was poured into about 4 l of purified water to take out a precipitate, which was to be a crude subject product, by filtration and the precipitate was dried under reduced pressure (yield: 90% (37 g)). The resulting precipitate was recrystallized from acetone to obtain diethyl isophthalate carrying cyanobiphenyl through a hexyl group as a target product (yield: 73% (30 g)). The resulting compound was subjected to nuclear magnetic resonance (NMR) measurement. The results of measurement are shown below. Also, the compound was subjected to mass spectrometry, with the result that a peak corresponding to a molecular weight of 515.6 was confirmed.

Aufarbeitung

  1. customthe mixture was reacted
  2. temperatureunder reflux for 24 hours
  3. temperatureto cool
  4. filtrationby filtration
  5. customthe precipitate was dried under reduced pressure (yield: 90% (37 g))
  6. customThe resulting precipitate was recrystallized from acetone

Quellen und Nachweise

ORD-Eintrag
ord-4b66bd81feb74d5f85c175b33f2e7d3a
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07501210B2

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