Salicylic Acid → Aspirin

HRID 1178048Notes

Reaction equation

HRID 1178048 reaction equation
N1C=CC=CC=1.[C:7]([OH:16])(=[O:15])[C:8]1[C:9](=[CH:11][CH:12]=[CH:13][CH:14]=1)[OH:10].[C:17](OC(=O)C)(=[O:19])[CH3:18]>C(Cl)Cl>[C:17]([O:10][C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[C:7]([OH:16])=[O:15])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 338Salicylic AcidHCID 1049PyridineHCID 7918Acetic Anhydride

Product 1

HCID 2244AspirinYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (64 μl, 0.80 mmol) was added to an ice cooled mixture of salicylic acid (10 mg, 0.72 mmol) and methylene chloride (10 mL). After 5 minutes, acetic anhydride (10 μl, 1.09 mmoles) was added. The resulting mixture was stirred at room temperature for 4 hrs. The product was extracted with methylene chloride and water. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford 2-acetoxybenzoic acid in 76% yield.

Workup

  1. temperaturecooled
  2. extractionThe product was extracted with methylene chloride and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-554541e1f28f476d9ed9cf5c41144fe2
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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