Acetyl chloride → 4-Methylacetanilide

HRID 522459Notes

Reaction equation

HRID 522459 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:15](Cl)(=[O:17])[CH3:16]>C(OCC)(=O)C.O>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:15]([CH3:16])=[O:17])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 7813p-ToluidineHCID 11430Potassium Carbonate

Product 1

HCID 76844-MethylacetanilideYield 77,801.203%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

100 g (933.3 mmol) of p-toluidine and 154.8 g (1.120 mmol) of potassium carbonate were dissolved in a mixed solvent of 1,000 ml of ethyl acetate and 500 ml of water. Thereinto was dropped 87.9 g (1.120 mmol) of acetyl chloride with ice-cooling, followed by stirring for 2 hours. Extraction with ethyl acetate was carried out. The organic phase obtained was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The crude crystal obtained was washed with hexane to obtain 130 g (yield: 93%) of p-acetotoluidine.

Workup

  1. temperaturecooling
  2. extractionExtraction with ethyl acetate
  3. customThe organic phase obtained
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe crude crystal obtained
  7. washwas washed with hexane

Sources & evidence

ORD record
ord-4ff9ca33039142979f62bc58ec950457
Source dataset
uspto-grants-2016_05
Patent number
US09332754B2

Reaction notes

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