Acetic Acid → N-Acetyl-2,6-xylidine

HRID 579968

Reaction equation

HRID 579968 reaction equation
[NH2:1][C:2]1[C:3]([CH3:9])=[CH:4][CH:5]=[CH:6][C:7]=1[CH3:8].[C:10](OC(=O)C)(=[O:12])[CH3:11].C(O)(=O)C>O>[C:10]([NH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9])(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 68962,6-DimethylanilineHCID 7918Acetic Anhydride

Product 1

HCID 16616N-Acetyl-2,6-xylidineYield 92.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 25 ml of 2,6-xylidine (0.20 mole) was added slowly a mixture of 25 ml of acetic anhydride (0.26 mole) and 25 ml of acetic acid (0.44 mole) under stirring at room temperature. The mixture was stirred for 30 minutes at room temperature and, then, diluted with water. The crystalline precipitate was collected by filtration to give 30.1 g (91%) of the title compound (m.p. 182°-184° C.; colorless needles).

Workup

  1. stirringThe mixture was stirred for 30 minutes at room temperature
  2. filtrationThe crystalline precipitate was collected by filtration

Sources & evidence

ORD record
ord-65932ea602734fb29d525f9b6ee3ee14
Source dataset
uspto-grants-1988_06
Patent number
US04751232

Linked notes

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