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

HRID 5295
Notes
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Reaction equation

HRID 5295 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6212ChloroformSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c2d3f9dc48864913be85c1333e2753ce
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05244771

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes