4,4'-Dimethoxybenzophenone → n-Hydroxy-1,1-bis(4-methoxyphenyl)methanimine

HRID 1591363Notes

Reaction equation

HRID 1591363 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=O)=[CH:5][CH:4]=1.Cl.[NH2:20][OH:21].[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7](=[N:20][OH:21])[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 70324,4'-DimethoxybenzophenoneHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 289718n-Hydroxy-1,1-bis(4-methoxyphenyl)methanimineYield 93.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

242 g (1 mole) of 4,4'-dimethoxybenzophenone was suspended in 2,000 ml of ethanol and 210 g (3 mole) of hydroxylamine hydrochloride and 300 ml (3 mole) of a 10N aqueous solution of NaOH were added thereto. Then the obtained mixture was heated under reflux. After two or thee hours, the ethanol was distilled off in vacuo and then a saline solution was added thereto followed by extracting with chloroform. The chloroform phase was washed with water and dried over magnesium sulfate. After distilling the chloroform off, the residue was recrystallized from ethanol. Thus 240 g of the title compound was obtained in the form of colorless needles.

Workup

  1. temperatureThen the obtained mixture was heated
  2. temperatureunder reflux
  3. distillationAfter two or thee hours, the ethanol was distilled off in vacuo
  4. additiona saline solution was added
  5. extractionby extracting with chloroform
  6. washThe chloroform phase was washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationAfter distilling the chloroform off, the residue
  9. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-aa571b17a9154eb2ac89a3554a99ebfa
Source dataset
uspto-grants-1993_04
Patent number
US05206403

Reaction notes

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