Salicylic Acid → Aspirin

HRID 1984996Notes

Reaction equation

HRID 1984996 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[C:11](OC(=O)C)(=[O:13])[CH3:12]>>[C:11]([O:4][C:3]1[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([OH:10])=[O:9])(=[O:13])[CH3:12]

Participants

3

Reactant 2

HCID 338Salicylic Acid2×HCID 7918Acetic Anhydride

Product 1

HCID 2244Aspirin

Conditions

Temperature
90 °C

Procedure

0.0072 moles of salicylic acid and 0.029 moles acetic anhydride (molar ratio=1:4) were taken in a 20 ml reaction vessel of reaction station. Nano-crystalline sulfated zirconia catalyst (SZ-1), activated at 450° C. in static air with salicylic acid to catalyst weight ratio 10:1, was added and the mixture was heated at 90° C. for 30 minutes. The reaction mixture was filtered to separate the catalyst. The acetyl salicylic acid was crystallized from the reaction mixture. The crude yield of acetyl salicylic acid obtained was 75%. It was further re-crystallized with ethanol-water to obtain pure crystals of acetyl salicylic acid and was characterized by melting point, FT-IR, and NMR spectroscopy.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. customto separate the catalyst
  4. customThe acetyl salicylic acid was crystallized from the reaction mixture

Sources & evidence

ORD record
ord-07bfd88e7b0940b49badd41058bba237
Source dataset
uspto-grants-2009_06
Patent number
US07544831B2

Reaction notes

Loading…