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HCID 14937397, Verbindung → HCID 15399808, Verbindung

HRID 2120022
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Reaktionsgleichung

Reaktionsgleichung von HRID 2120022
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])(=O)C.[CH2:18]([O:24][C:25]1[CH:26]=[C:27]([C:38]2[CH:43]=[CH:42][C:41]([O:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[C:40]([O:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH:39]=2)[CH:28]=[CH:29][C:30]=1[O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>ClCCl.[Fe](Cl)Cl>[OH:4][C:5]1[C:6]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:7][C:8]2[C:43]3[C:38](=[CH:39][C:40]([O:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])=[C:41]([O:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH:42]=3)[C:27]3[C:28](=[CH:29][C:30]([O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[C:25]([O:24][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:26]=3)[C:9]=2[CH:10]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 14937397HCID 14937397, VerbindungHCID 23437329HCID 23437329, Verbindung

Produkt 1

HCID 15399808HCID 15399808, VerbindungAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24458Ferrous ChlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Anhydrous iron chloride (4.7 g, 28.9 mmol) was added to a stirred mixture of 2-acetoxy-1-hexyloxybenzene (3.4 g, 14.4 mmol) and 3,3′,4,4′-tetrahexyloxybiphenyl (4.0 g, 7.2 mmol) in dichloromethane. The mixture was stirred for 5 h and poured onto methanol (300 ml). The resultant precipitate was filtered off and saponified with potassium carbonate in ethanol (5% water) under reflux for over night. After cooling, water (50 ml) was added and the product was extracted with dichloromethane, dried (MgSO4), concentrated and purified by column chromatography on silica gel using dichloromethane and petroleum spirit (1:1) as eluent and then recrystallised from ethanol to yield a white solid (3.59 g, 67%). Found: C, 77.30; H, 9.85. C48H72O6 requires C, 77.38; H, 9.74. δH (CHCl3) 7.96 (s, 1H, ArH), 7.83-7.82 (m, 4H, ArH), 7.77 (s, 1H, ArH), 5.92 (1H, s, OH), 4.31-4.18 (m, 10H, OCH2), 1.99-1.92 (m, 10H, CH2), 1.58-1.55 (m, 10H, CH2), 1.46-1.38 (m, 20H, CH2), 0.97-0.83 (15H, m, CH3).

Aufarbeitung

  1. additionpoured onto methanol (300 ml)
  2. filtrationThe resultant precipitate was filtered off
  3. temperatureunder reflux for over night
  4. temperatureAfter cooling
  5. additionwater (50 ml) was added
  6. extractionthe product was extracted with dichloromethane
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. custompurified by column chromatography on silica gel
  10. customrecrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-2bd98c1d2c6d4a1693d27025ae786f9c
Quelldatensatz
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06689290B2

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