Acetyl chloride → N-(4-acetyl-3-hydroxyphenyl)acetamide

HRID 54588Notes

Reaction equation

HRID 54588 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([O:11]C)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[Al+3].[Cl-].[Cl-].[Cl-].[C:17](Cl)(=[O:19])[CH3:18]>ClCCCl>[C:17]([C:8]1[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][C:7]=1[OH:11])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11494Acetamide, N-(3-methoxyphenyl)-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 2775185N-(4-acetyl-3-hydroxyphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

67.5 g (0.41 mol)3-acetamidoanisol are suspended in 200 ml 1,2-dichloroethane and cooled in an ice bath. 217 g (1.64 mol) AlCl3 and after it 38.5 g (0.49 mol) acetylchloride were added successively. Stirring was continued 1/2 hour. After 5 hours the reaction was quenched with ice and ethylacetate and water were added. The organic layer was seperated, washed with water, dried over MgSO4 and concentrated in vacuo. The residue was recrystallized from dioxane and water.

Workup

  1. temperaturecooled in an ice bath
  2. customAfter 5 hours the reaction was quenched with ice and ethylacetate and water
  3. additionwere added
  4. customThe organic layer was seperated
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was recrystallized from dioxane and water

Sources & evidence

ORD record
ord-cad2b301689e4acc8c686d1eb3ec0758
Source dataset
uspto-grants-1997_04
Patent number
US05622989

Reaction notes

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