2-[Bis(4-acetoxyphenyl)methyl]-N-(2,4-dimethoxyphenyl)benzamide → 2-[bis(4-hydroxyphenyl)methyl]-N-(2,4-dimethoxyphenyl)benzamide

HRID 1196156Notes

Reaction equation

HRID 1196156 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:31]2[CH:36]=[CH:35][C:34]([O:37]C(=O)C)=[CH:33][CH:32]=2)[C:12]2[CH:30]=[CH:29][CH:28]=[CH:27][C:13]=2[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[O:25][CH3:26])=[O:15])=[CH:7][CH:6]=1)(=O)C>C(=O)([O-])O.[Na+].CO>[OH:37][C:34]1[CH:35]=[CH:36][C:31]([CH:11]([C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:10][CH:9]=2)[C:12]2[CH:30]=[CH:29][CH:28]=[CH:27][C:13]=2[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[O:25][CH3:26])=[O:15])=[CH:32][CH:33]=1

Participants

4

Reactant 1

HCID 152967812-[Bis(4-acetoxyphenyl)methyl]-N-(2,4-dimethoxyphenyl)benzamide

Product 1

HCID 152967822-[bis(4-hydroxyphenyl)methyl]-N-(2,4-dimethoxyphenyl)benzamideYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

In a mixture of 50 ml of saturated aqueous sodium hydrogencarbonate solution and 50 ml of methanol was suspended 2.6 g of Compound 2 prepared in Example 1, and the suspension was heated under reflux for 30 minutes. The resulting mixture was concentrated under reduced pressure, and water was added to the residue. The resulting mixture was extracted with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was recrystallized to afford 1.23 g of the desired product.

Workup

  1. temperaturethe suspension was heated
  2. temperatureunder reflux for 30 minutes
  3. concentrationThe resulting mixture was concentrated under reduced pressure, and water
  4. additionwas added to the residue
  5. extractionThe resulting mixture was extracted with ethyl acetate
  6. dry with materialthe extract was dried over anhydrous magnesium sulfate
  7. concentrationAfter concentration under reduced pressure
  8. customthe residue was recrystallized

Sources & evidence

ORD record
ord-323bf0b8430f4777865591ac082d1188
Source dataset
uspto-grants-1992_05
Patent number
US05112867

Reaction notes

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