Salsalate → Acetylsalicylsalicylic acid

HRID 705406Notes

Reaction equation

HRID 705406 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([OH:19])=[C:5]([C:7]([O:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=2[C:16]([OH:18])=[O:17])=[O:8])[CH:6]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>OS(O)(=O)=O>[C:20]([O:19][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=1[C:7]([O:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=1[C:16]([OH:18])=[O:17])=[O:8])(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 5161SalsalateHCID 7918Acetic Anhydride

Product 1

HCID 10745Acetylsalicylsalicylic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a solution of salsalicylic acid (salsalate) (5.0 g, 19.37 mmol) in acetic anhydride (15.0 mL, 147.0 mmol) was added 3 drops of conc. H2SO4 and the mixture was stirred at RT for 16-20 h. The mixture was diluted with ice cold water (50 mL) and precipitated solid was filtered, washed with water (2×10 mL), hexanes (20 mL) and dried to afford 2-{[2-(acetyloxy)benzoyl]oxy}benzoic acid, 11 (5.5 g, mmol) as white solid. Rf: 0.3 (50% EtOAc/hexanes).

Workup

  1. customprecipitated solid
  2. filtrationwas filtered
  3. washwashed with water (2×10 mL), hexanes (20 mL)
  4. customdried

Sources & evidence

ORD record
ord-95109dfab47d400b83e6c9bc6ba01d48
Source dataset
uspto-grants-2015_11
Patent number
US09174931B2

Reaction notes

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