Acetic Anhydride → 3-Acetamido-4-methylbenzoic acid

HRID 1672475Notes

Reaction equation

HRID 1672475 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].[CH3:12][C:13](OC(C)=O)=[O:14]>C(O)(=O)C>[C:13]([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])[CH3:12]

Participants

4

Reactant 2

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

Product 1

HCID 2434323-Acetamido-4-methylbenzoic acidYield 87.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-amino-4-methylbenzoic acid (375 g, 2.48 mol) in glacial acetic acid (2500 mL) was added dropwise Ac2O (1547.7 g, 15.2 mol). After the addition, the reaction mixture was stirred at room temperature overnight. The solid formed was collected by filtration, and washed with acetic acid (500 mL×2) and ether (500 mL×2). Then the solid was dried in vacuo to give the title compound (420 g, 87.6%) as an off-white solid.

Workup

  1. additionAfter the addition
  2. customThe solid formed
  3. filtrationwas collected by filtration
  4. washwashed with acetic acid (500 mL×2) and ether (500 mL×2)
  5. customThen the solid was dried in vacuo

Sources & evidence

ORD record
ord-6d967069080e4f20b4ade33433b0f07a
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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