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

HRID 962708

Reaction equation

HRID 962708 reaction equation
[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

Participants

8

Reactant 5

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

Product 1

HCID 49622034-[Amino(phenyl)methyl]phenol

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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 and with a 3% by volume solution of methanol in ethyl acetate
  4. customto give
  5. custom2.74 g of the title compound as crystals, melting at 113°-115° C. (after recrystallization from methylene chloride)

Sources & evidence

ORD record
ord-7da5bf70670f46659e1bfa728624145f
Source dataset
uspto-grants-1998_06
Patent number
US05760025

Linked notes

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