3-Hydroxybenzyl alcohol → Aspirin

HRID 2122062Notes

Reaction equation

HRID 2122062 reaction equation
[OH:1]CC1C=C(O)C=CC=1.C(=O)([O-])[O-].[K+].[K+].[C:16]([O:19][C:20]1[C:21](=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:22](Cl)=[O:23])(=[O:18])[CH3:17]>CC(C)=O>[C:16]([O:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22]([OH:1])=[O:23])(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 1023-Hydroxybenzyl alcoholHCID 11430Potassium CarbonateHCID 796682-Acetoxybenzoyl chloride

Product 1

HCID 2244AspirinYield 91%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

3-hydroxymethylphenol (10 g, 0.08 moles) is dissolved in acetone (50 ml). In the obtained solution potassium carbonate in powder (22.2 g, 0.16 moles) is suspended. To the suspension an acetylsalicylic acid chloride solution (16 g, 0.08 moles) in acetone (50 ml) is added at a temperature of 5°-10° C. under stirring. The mixture is maintained at a temperature in the above mentioned range, under stirring, for 2 hours, then filtered and the solvent evaporated under vacuum. The residue is crystallized from isopropanol. 3-hydroxymethylphenyl ester of the 2-acetoxy-benzoic acid (21.0 g, 0.07 moles, yield 91%) is obtained.

Workup

  1. temperatureThe mixture is maintained at a temperature in the
  2. stirringunder stirring, for 2 hours
  3. filtrationfiltered
  4. customthe solvent evaporated under vacuum
  5. customThe residue is crystallized from isopropanol

Sources & evidence

ORD record
ord-56716f63891c43799a268840d1d07b7c
Source dataset
uspto-grants-2004_02
Patent number
US06696591B1

Reaction notes

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