Succinic anhydride → 4-(4'-Methoxy-biphenyl-4-yl)-4-oxo-butyric acid

HRID 1856511

Reaktionsgleichung

Reaktionsgleichung von HRID 1856511
[OH:1][CH:2]([C:8]1(O)[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH2:9]1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH3:21][O:22]C1C=CC(C2C=CC=CC=2)=CC=1.C1(=O)OC(=O)CC1.[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C1C=CC=CC=1)([O-])=O>[CH3:21][O:22][C:17]1[CH:18]=[CH:19][C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:2](=[O:1])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])=[CH:9][CH:10]=2)=[CH:15][CH:16]=1

Komponenten

6

Edukt 4

HCID 7922Succinic anhydrideHCID 119434-MethoxybiphenylHCID 6451240Aluminum(III) ChlorideHCID 86737169gamma,4-Dihydroxy-4-biphenylbutyric acid

Produkt 1

HCID 230052384-(4'-Methoxy-biphenyl-4-yl)-4-oxo-butyric acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7416NitrobenzeneLösungsmittel

Versuchsvorschrift

γ,4-dihydroxy-4-biphenylbutyric acid may be prepared by treating p-methoxybiphenyl with succinic anhydride in nitrobenzene. The mixture is treated with aluminum chloride at reduced temperature. The solid is dissolved in aqueous base with heat, chilled to reprecipitate and acidified giving 4'-methoxy-γ-oxo-4-biphenylbutyric acid. This intermediate is refluxed with hydrogen bromide for several hours, diluted with water and cooled. The precipitate is 4'-hydroxy-γ-oxo-biphenylbutyric acid. This intermediate is treated with sodium borohydride in an alkaline medium and then acidified giving the desired product.

Aufarbeitung

  1. dissolutionThe solid is dissolved in aqueous base
  2. temperaturewith heat
  3. temperaturechilled

Quellen und Nachweise

ORD-Eintrag
ord-86956048702143539d2b0518aac199fd
Quelldatensatz
uspto-grants-1980_08
Patentnummer
US04219668

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