Sodium Hydroxide → 4-[Amino(phenyl)methyl]phenol

HRID 1735561

Reaktionsgleichung

Reaktionsgleichung von HRID 1735561
[OH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6](=[N:13]O)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+].[OH-].[Na+]>[Cl-].[Cl-].[Cl-].[Ti+3].C(OCC)(=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([NH2:13])[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:15][CH:16]=1

Komponenten

8

Edukt 5

HCID 14798Sodium HydroxideHCID 973924-Hydroxybenzophenone oximeHCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 49622034-[Amino(phenyl)methyl]phenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10313229titanium(III) trichlorideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A procedure similar to that described in Preparation 12 was repeated, but using 86 ml of a methanolic solution containing 4.28 g of 4-hydroxybenzophenone oxime, 17.03 g of ammonium acetate, 3.79 g of sodium cyanoborohydride, and 40.1 ml of a 17-19% by volume aqueous solution of titanium trichloride, and using a dilute aqueous solution of sodium hydrogencarbonate instead of the aqueous solution of sodium hydroxide, and using ethyl acetate as the extracting solvent. The residue obtained was subjected to silica gel column chromatography and eluted with a 80% by volume solution of ethyl acetate in hexane, with ethyl acetate itself, and with a 3% by volume solution of methanol in ethyl acetate, to give 2.74 g of the title compound as crystals, melting at 113° -115° C. (after recrystallization from methylene chloride).

Aufarbeitung

  1. customA procedure similar to that described in Preparation 12
  2. customThe residue obtained
  3. washeluted with a 80% by volume solution of ethyl acetate in hexane, with ethyl acetate itself
  4. customwith a 3% by volume solution of methanol in ethyl acetate, to give
  5. custom2.74 g of the title compound as crystals, melting at 113° -115° C. (after recrystallization from methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-9d77e4a05f154148825ad8a8d05fd715
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05536714

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