Acetyl chloride → 4-Acetamido-3-chlorobenzoic acid

HRID 1861253Notes

Reaction equation

HRID 1861253 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[Cl:11].[C:12](Cl)(=[O:14])[CH3:13]>C1COCC1>[C:12]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[Cl:11])(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 172114-Amino-3-chlorobenzoic acid

Product 1

HCID 6809514-Acetamido-3-chlorobenzoic acidYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-amino-3-chloro-benzoic Acid (10.0 g, 58.3 mmol) in anhydrous THF (100 mL) was added acetyl chloride (20.7 ml, 291.1 mmol) and the solution stirred at room temperature for 48 hours. The solvent was evaporated and the product precipitated from hexanes then filtered and dried to give a white solid (11.73 g, 94% yield). 1H-NMR (500 MHz, CD3OD) δ 2.28 (s, 3H), 7.92 (dd, 1H), 7.99-8.16 (m, 2H). Analytical HPLC (cyano column) 7.84 min.

Workup

  1. customThe solvent was evaporated
  2. customthe product precipitated from hexanes
  3. filtrationthen filtered
  4. customdried

Sources & evidence

ORD record
ord-a33c50123d334712b7b52f7b58d2b63b
Source dataset
uspto-grants-2003_03
Patent number
US06531474B1

Reaction notes

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