Acetic Acid → 1,4-Bis(p-octyloxybenzylidene amino)anthraquinone

HRID 262413

Reaktionsgleichung

Reaktionsgleichung von HRID 262413
[C:1]([OH:4])(=O)[CH3:2].[NH2:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:21])[C:10]=2[C:9]([NH2:22])=[CH:8][CH:7]=1.[CH2:23]([O:31][C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CO>[CH2:30]([O:4][C:1]1[CH:2]=[CH:36][C:35]([CH:38]=[N:5][C:6]2[C:19]3[C:18](=[O:20])[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11](=[O:21])[C:10]=3[C:9]([N:22]=[CH:36][C:35]3[CH:38]=[CH:39][C:32]([O:31][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:33][CH:34]=3)=[CH:8][CH:7]=2)=[CH:34][CH:33]=1)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH3:23]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 31420Disperse Violet 1HCID 90358p-(Octyloxy)benzaldehyde

Produkt 1

HCID 201633371,4-Bis(p-octyloxybenzylidene amino)anthraquinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In a round-bottomed flask fitted with thermometer, reflux condenser and stirrer is placed a mixture of 25 ml. glacial acetic acid and 50 ml methanol and in it is dissolved 2.38 g (0.1 mol) 1,4-diaminoanthraquinone. There is then added 4.68 g (0.2 mol) p-octyloxybenzaldehyde and the mixture is heated at 90° for one hour. The reaction mixture is cooled to about 20°-25° and poured into ice water. The precipitated product is collected and recrystallized from ethylene glycol monomethyl ether or 1:1 methanol water as small purple needles. The crystallization is repeated twice more to obtain 1,4-bis(p-octyloxybenzylidene amino)anthraquinone m.b. 280° (dec) having absorption spectra in visual and infra red ranges as shown in FIGS. 9, 10 and 11 and of sufficient purity for use in guest-host combinations. Analysis: Calculated for C44H54N2O4 ; 78.3%C, 8.06%H, 4.15%N: found 77.61%C, 7.46%H, 4.18%N.

Aufarbeitung

  1. customIn a round-bottomed flask fitted with thermometer
  2. temperaturereflux condenser and stirrer
  3. additiona mixture of 25 ml
  4. temperaturethe mixture is heated at 90° for one hour
  5. temperatureThe reaction mixture is cooled to about 20°-25°
  6. customThe precipitated product is collected
  7. customrecrystallized from ethylene glycol monomethyl ether or 1:1 methanol water as small purple needles
  8. customThe crystallization

Quellen und Nachweise

ORD-Eintrag
ord-f38bff32a5214b7ebffd4cff8b27f0aa
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04154746

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