Acetic Anhydride → 3-Acetamido-4-methylbenzoic acid

HRID 968789

Reaction equation

HRID 968789 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[C:12](OC(=O)C)(=[O:14])[CH3:13]>C(O)(=O)C>[C:12]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6])(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 755683-Amino-4-methylbenzoic acid

Product 1

HCID 2434323-Acetamido-4-methylbenzoic acidYield 76%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-amino-4-methylbenzoic acid (13) (27.23 g, 180.2 mmol) and acetic acid (190 mL) is heated to 60° C., and acetic anhydride (120 mL, 1300 mmol) is introduced to the reaction mixture over about 0.25 hours. The reaction mixture is then heated to reflux and stirred for about 30 minutes. The mixture is then cooled to room temperature, and the solid obtained is filtered, washed with water (100 mL), and dried to provide 3-(Acetylamino)-4-methylbenzoic Acid (14) as a light pink colored solid (26.37 g, 76% Yield).

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureto reflux
  3. temperatureThe mixture is then cooled to room temperature
  4. customthe solid obtained
  5. filtrationis filtered
  6. washwashed with water (100 mL)
  7. customdried

Sources & evidence

ORD record
ord-5656d06a0eba4b70abe4bfc0449c877a
Source dataset
uspto-grants-2007_12
Patent number
US07304084B2

Linked notes

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