4-Methoxy-1-naphthol → 4,4'-Dimethoxy[2,2'-binaphthalene]-1,1'-diol

HRID 5295

Reaktionsgleichung

Reaktionsgleichung von HRID 5295
COC1C2C(=CC=CC=2)C(O)=CC=1.[CH3:14][O:15][C:16]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:32](=[O:33])/[C:18](=[C:19]2\[CH:20]=[C:21]([O:30][CH3:31])[C:22]3[C:27]([C:28]\2=[O:29])=[CH:26][CH:25]=[CH:24][CH:23]=3)/[CH:17]=1>[Ag]=O.C(Cl)(Cl)Cl>[CH3:31][O:30][C:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28]([OH:29])=[C:19]([C:18]2[CH:17]=[C:16]([O:15][CH3:14])[C:39]3[C:34]([C:32]=2[OH:33])=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:20]=1

Komponenten

5

Edukt 2

HCID 665424-Methoxy-1-naphtholHCID 53788141(2H)-Naphthalenone, 4-methoxy-2-(4-methoxy-1-oxo-2(1H)-naphthalenylidene)-

Produkt 1

HCID 132842994,4'-Dimethoxy[2,2'-binaphthalene]-1,1'-diol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 92152Silver(II) oxideKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Under an atmosphere of nitrogen, a mixture of 5.0 g of 4-methoxy-1-naphthol and 50 mL chloroform was mechanically stirred with 10.0 g silver oxide until the conversion to Russig's Blue was complete. The unreacted silver oxide was filtered and washed with chloroform. The filtrate and chloroform washings were combined and stirred with 4.9 g of 4-methoxy-1-naphthol until the solution turned gray. The solution was then concentrated to 50 mL and the resulting precipitate was filtered, washed with chloroform and dried to yield 3.18 g of 1,1'-dimethoxy-3,3'-binaphthyl-4,4'-diol as a light gray solid. The structure was confirmed by NMR.

Aufarbeitung

  1. filtrationThe unreacted silver oxide was filtered
  2. washwashed with chloroform
  3. concentrationThe solution was then concentrated to 50 mL
  4. filtrationthe resulting precipitate was filtered
  5. washwashed with chloroform
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c2d3f9dc48864913be85c1333e2753ce
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244771

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