p-Toluidine → 4-Methylacetanilide

HRID 1459125Notes

Reaction equation

HRID 1459125 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10]>>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:9](=[O:11])[CH3:10])=[CH:3][CH:4]=1

Participants

3

Reactant 2

HCID 7813p-ToluidineHCID 7918Acetic Anhydride

Product 1

HCID 76844-MethylacetanilideYield 97%

Procedure

Into three neck round bottom flask (5 L) equipped with a mechanical stirrer, a condenser, and an addition funnel, were added p-toluidine (995 grams, 9.3 mol) and hexanes (1.6 L). Acetic anhydride (960 mL, 10.2 mol) was added dropwise for 2 hour enough to reflux. Then it was refluxed for 1 hour and cooled to room temperature to give a brown solid. This was collected by suction filtration, transferred into a beaker, and washed with water (2 L) for 30 minutes. The filtration and washing procedures were repeated. The wet white crystals was air dried for 7 days to N-(4-Methylphenyl)acetamide (1,343 g, 97% yield). Melting point: 150-152° C. (Lit. 153° C., Merck Index 11, 67).

Workup

  1. customInto three neck round bottom flask (5 L) equipped with a mechanical stirrer, a condenser, and an addition funnel
  2. temperatureto reflux
  3. temperatureThen it was refluxed for 1 hour
  4. customto give a brown solid
  5. filtrationThis was collected by suction filtration
  6. washwashed with water (2 L) for 30 minutes
  7. filtrationThe filtration
  8. washwashing procedures

Sources & evidence

ORD record
ord-717c8d88b5d04575bb80a5bbc14864f2
Source dataset
uspto-grants-1998_12
Patent number
US05853906

Reaction notes

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