p-Anisoyl chloride → HCID 18174608, compound

HRID 427656Notes

Reaction equation

HRID 427656 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[OH-:10].[Na+].[CH3:12][O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>C(Cl)Cl>[CH3:12][O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([O:10][O:9][C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([NH:8][C:18](=[O:19])[C:17]3[CH:21]=[CH:22][C:14]([O:13][CH3:12])=[CH:15][CH:16]=3)[C:2]=2[NH:1][C:18](=[O:19])[C:17]2[CH:21]=[CH:22][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)=[O:19])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 14798Sodium HydroxideHCID 5799372,3-Diaminophenol

Product 1

HCID 18174608HCID 18174608, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3-Diaminophenol (2.48g, 20 mmol) was dissolved in methylene chloride (200 mL) and the solution was cooled to ice-water bath temperature. Aqueous 5 N sodium hydroxide solution (126 mL) was added followed by 4-methoxybenzoyl chloride (8.6 mL, 63 mmol). The mixture was allowed to warm to room temperature and stirred for 18 h. The organic layer was separated and washed with dilute aqueous sodium hydroxide solution, dilute aqueous hydrochloric acid, and saturated aqueous sodium chloride solution. The organic layer was dried (sodium sulfate), filtered, and concentrated in vacuo to give 7.75 g (74%) of the title compound as a brown foam. This material was used without further purification.

Workup

  1. temperaturethe solution was cooled to ice-water bath temperature
  2. customThe organic layer was separated
  3. washwashed with dilute aqueous sodium hydroxide solution, dilute aqueous hydrochloric acid, and saturated aqueous sodium chloride solution
  4. dry with materialThe organic layer was dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ef2793f9aad8472da56d5ec58903f1a0
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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