Acetic Acid → O-acetyl-5-chlorosalicylic acid

HRID 644789Notes

Reaction equation

HRID 644789 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13].C(O)(=O)C>S(=O)(=O)(O)O>[C:12]([O:8][C:7](=[O:9])[C:6]1[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=1)[OH:11])(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 94475-Chlorosalicylic Acid

Product 1

HCID 86592304O-acetyl-5-chlorosalicylic acidYield 76%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
70 °C

Procedure

5-Chlorosalicylic acid (17.3 g, 100 mmol) and three drops of concentrated sulfuric acid (98%) were added to a solution of acetic anhydride (14 g, 137 mmol) and glacial acetic acid (16.4 g, 274 mmol) with stirring. The reaction mixture was slowly heated to 70° C. and stirred for 2 hours. The reaction mixture was cooled to room temperature and was gradually added to ice water (500 mL) to precipitate the acetylated product. These solids were collected and washed with water. The two batches of product were combined and recrystallized in ethyl acetate. The pure crystals were collected via vacuum filtration to give 16.3 g of O-acetyl-5-chlorosalicylic acid (76 mmol, 76% yield).

Workup

  1. stirringstirred for 2 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customto precipitate the acetylated product
  4. customThese solids were collected
  5. washwashed with water
  6. customrecrystallized in ethyl acetate
  7. filtrationThe pure crystals were collected via vacuum filtration

Sources & evidence

ORD record
ord-ed093e96ccae4adfb3a625289049055f
Source dataset
uspto-grants-2010_04
Patent number
US07700775B2

Reaction notes

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