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

HRID 1871627Notes

Reaction equation

HRID 1871627 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

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-afbf0230e9b1475897da3d7b3f058040
Source dataset
uspto-grants-2000_08
Patent number
US06103912

Reaction notes

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