Sodium Hydroxide → 114331-87-2

HRID 395800Notes

Reaction equation

HRID 395800 reaction equation
COC1C=CC(C([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17](=[O:26])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=O)=CC=1.[OH-].[Na+]>CO>[OH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17](=[O:26])[C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14064886HCID 14064886, compound

Product 1

HCID 483826114331-87-2Yield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-[2-(4-methoxybenzoyloxy)phenyl]-4-methoxybenzamide (3.0 g, 8.0 mmol) in methanol (50 mL) was treated with 5 N aqueous sodium hydroxide (4.78 mL) at room temperature for 16 h. The solution was concentrated to one-half volume in vacuo, 5 N aqueous sodium hydroxide was added, and the resulting mixture stirred for an additional 16 h. The mixture was concentrated in vacuo and acidified with dilute hydrochloric acid. The resulting precipitate was collected by filtration, dissolved in ethyl acetate, and extracted with saturated aqueous potassium carbonate solution. The aquous layer was acidified with dilute hydrochloric acid and extrated with ethyl acetate. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo to provide 1.75 g (90%) the title product as a crystalline solid.

Workup

  1. concentrationThe solution was concentrated to one-half volume in vacuo, 5 N aqueous sodium hydroxide
  2. additionwas added
  3. concentrationThe mixture was concentrated in vacuo
  4. filtrationThe resulting precipitate was collected by filtration
  5. dissolutiondissolved in ethyl acetate
  6. extractionextracted with saturated aqueous potassium carbonate solution
  7. dry with materialThe organic layer was dried (magnesium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a5fbdc04a49b42a1b5978de1ba642321
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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