Aspirin → Aspirin sodium

HRID 1415285Notes

Reaction equation

HRID 1415285 reaction equation
O.C(=O)([O-])[O-].[Na+:6].[Na+].[CH3:8][C:9]([O:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=1[C:18]([OH:20])=[O:19])=[O:10]>O>[C:9]([O:11][C:12]1[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:18]([O-:20])=[O:19])(=[O:10])[CH3:8].[Na+:6]

Participants

4

Reactant 2

HCID 2244AspirinHCID 2735133Sodium Carbonate Monohydrate

Product 1

HCID 23666729Aspirin sodium

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A cold solution (10° C.) of sodium acetylsalicylate was prepared by adding 34.6 gms. of sodium carbonate hydrate and 100 gms. of aspirin to 600 ml. of distilled water stirring until all solids had dissolved and using an additional 320 ml. of distilled water to wash down the walls of the container. Twenty-five gms. of instant tea was added with stirring until the tea dissolved. To 750. ml. of cold distilled water (5° C.) was added 250 ml. of the aspirin-tea solution and 20 ml. of glacial acetic acid. After a period of one hour the remaining aspirin-tea solution was added in 50 ml. portions with glacial acetic acid being added after each addition, the first amount being 4.0 ml. and increasing each addition by 1.0 ml.; a stirring period of 10 minutes occurred between each addition. The coprecipitate was allowed to settle, the supernatant was decanted, the coprecipitate was washed with glycine buffer solution and collected by filtration. After air drying, the product weighted 79.2 gms. Analysis of the coprecipitate showed it contained 95.3% aspirin, 4.17% tea constituent, 0.03% salicylic acid and 0.50% water.

Workup

  1. additionby adding 34.6 gms
  2. washof distilled water to wash down the walls of the container
  3. additionof instant tea was added
  4. dissolutiondissolved
  5. distillationof cold distilled water (5° C.)
  6. additionwas added 250 ml
  7. additionAfter a period of one hour the remaining aspirin-tea solution was added in 50 ml
  8. additionportions with glacial acetic acid being added
  9. additionafter each addition
  10. temperatureand increasing
  11. additioneach addition by 1.0 ml
  12. additiona stirring period of 10 minutes occurred between each addition
  13. customthe supernatant was decanted
  14. washthe coprecipitate was washed with glycine buffer solution
  15. filtrationcollected by filtration
  16. customAfter air drying

Sources & evidence

ORD record
ord-b6fbe22de48e40fcae6a3d280719948f
Source dataset
uspto-grants-1977_01
Patent number
US04003999

Reaction notes

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