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

HRID 1696965Notes

Reaction equation

HRID 1696965 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]>C(O)C.N1C=CC=CC=1>[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)=[N:20][OH:21])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 70324,4'-DimethoxybenzophenoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 289718n-Hydroxy-1,1-bis(4-methoxyphenyl)methanimine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

4,4′-Dimethoxybenzophenone (25 g, 103 mmol) is suspended in ethanol (150 ml) and pyridine (30 ml). Hydroxylamine hydrochloride (21.50 g, 310 mmol) is added and the reaction mixture is refluxed. The reaction is shown to be complete by TLC after 3 hours. The reaction mixture is allowed to cool and the solvent is removed in vacuo. The residue is partitioned between ethyl acetate (500 ml) and water (500 ml). The organic layer dried is over MgSO4, filtered and the solvent removed in vacuo. The title compound is obtained following crystallisation from ethylacetate/cyclohexane. 1H nmr (CDCl3, 400 MHz); 7.70(s, 1H), 7.40(d of d, 4H), 6.95(d, 2H), 6.85(d, 2H), 3.85(s, 3H), 3.80(s, 3H).

Workup

  1. temperaturethe reaction mixture is refluxed
  2. temperatureto cool
  3. customthe solvent is removed in vacuo
  4. customThe residue is partitioned between ethyl acetate (500 ml) and water (500 ml)
  5. customThe organic layer dried
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-8bd6f54d1722462c91a169b7bfce83cc
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

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