Salicylic Acid → Aspirin

HRID 1257481Notes

Reaction equation

HRID 1257481 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(O)(=O)C>[CH3:12][C:11]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9])=[O:13]

Participants

4

Reactant 2

HCID 338Salicylic AcidHCID 7918Acetic Anhydride

Product 1

HCID 2244Aspirin

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Commercially, aspirin is synthesized using a two-step process. Phenol, generally extracted from coal tar, is treated with sodium base to generate sodium phenoxide. Sodium phenoxide is then reacted with carbon dioxide under high temperature and pressure to yield salicylate, which is acidified to obtain salicylic acid. This process is known as the Kolbe-Schmitt reaction. Salicylic acid is acetylated with acetic anhydride to produce aspirin and acetic acid as byproduct.

Workup

  1. customThis process is known as the Kolbe-Schmitt reaction

Sources & evidence

ORD record
ord-72c311ce8dea41689de4d74d72468e40
Source dataset
uspto-grants-2013_06
Patent number
US08461377B2

Reaction notes

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