Water → Aspirin

HRID 2375549Notes

Reaction equation

HRID 2375549 reaction equation
[C:1]([O:4][C:5]1[C:6](=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:7](Cl)=[O:8])(=[O:3])[CH3:2].[OH2:14]>C1(C)C=CC=CC=1>[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:14])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 796682-Acetoxybenzoyl chloride

Product 1

HCID 2244AspirinYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
7.5 °C

Procedure

To the so obtained solution, a solution of the acetylsalicylic acid chloride (16 g, 0.08 moles) in toluene (50 ml) is added under stirring at the temperature of 5-10° C. The mixture is maintained at a temperature within the above range, under stirring for 2 hours, then poured into water and then extracted with dichloromethane (2×100 ml). The organic phase is separated, washed in sequence with a solution of potassium carbonate at 25% w/v, with water, with a 3% hydrochloric acid solution and finally again with water, then anhydrified with sodium sulphate and the solvent evaporated under reduced pressure. The residue is crystallized from isopropanol. 3-hydroxymethyl phenyl ester of the 2-acetoxybenzoic acid (45.8 g, 0.16 moles, yield 80%) is obtained.

Workup

  1. temperatureThe mixture is maintained at a temperature within the above range
  2. stirringunder stirring for 2 hours
  3. extractionextracted with dichloromethane (2×100 ml)
  4. customThe organic phase is separated
  5. washwashed in sequence with a solution of potassium carbonate at 25%
  6. customthe solvent evaporated under reduced pressure
  7. customThe residue is crystallized from isopropanol

Sources & evidence

ORD record
ord-4793d801c93a4c5494d3bed33fa1dd7e
Source dataset
uspto-grants-2008_12
Patent number
US07465803B2

Reaction notes

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