Aspirin → Salicylic Acid

HRID 262103Notes

Reaction equation

C(C1C=CC=CC=1[C:10]1[C:11]([O:19]C(=O)C)=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([O-:15])=[O:14])(=O)N.CC(OC1C=CC=CC=1C(O)=O)=O.[C:36]([NH2:45])(=[O:44])[C:37]1[C:38](=[CH:40][CH:41]=[CH:42][CH:43]=1)[OH:39]>>[C:13]([OH:15])(=[O:14])[C:12]1[C:11](=[CH:10][CH:18]=[CH:17][CH:16]=1)[OH:19].[C:36]([NH2:45])(=[O:44])[C:37]1[C:38](=[CH:40][CH:41]=[CH:42][CH:43]=1)[OH:39]

Participants

Reactant 3

HCID 2244Aspirin

HCID 5147Salicylamide

HCID 21319996HCID 21319996, compound2×

Product 2

HCID 338Salicylic Acid

HCID 5147Salicylamide

Procedure

The following experiments illustrate (A) the reduced gastric toxicity of 2-(carbamoyl)phenyl-2-acetoxybenzoate relative to a physical mixture of aspirin and salicylamide and (B) the in vivo hydrolysis of 2-(carbamoyl)phenyl-2-acetoxybenzoate to give plasma concentrations of salicylic acid and salicylamide.

Sources & evidence

ORD record: ord-2aba2e29f55c4639b0f13c47850e352e
Source dataset: uspto-grants-1979_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04153691

Reaction notes

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