Water → Ibuprofen, Sodium Salt

HRID 1449781Notes

Reaction equation

HRID 1449781 reaction equation
[OH:1][C:2]([CH:4]([C:6]1[CH:15]=[CH:14][C:9]([CH2:10][CH:11]([CH3:13])[CH3:12])=[CH:8][CH:7]=1)[CH3:5])=[O:3].O.[OH-].[Na+:18]>C1(C)C=CC=CC=1>[Na+:18].[O-:3][C:2]([CH:4]([C:6]1[CH:7]=[CH:8][C:9]([CH2:10][CH:11]([CH3:12])[CH3:13])=[CH:14][CH:15]=1)[CH3:5])=[O:1]

Participants

5

Reactant 3

HCID 962WaterHCID 3672Ibuprofen, (+-)-HCID 14798Sodium Hydroxide

Product 1

HCID 5338317Ibuprofen, Sodium Salt

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of (S)-enriched ibuprofen having an enantiomeric purity of 95.5% (211 kg) in toluene (797 kg) was heated to 60° C. with water (300 l) and aqueous sodium hydroxide solution (52 l--specific gravity 1.5) and allowed to settle for four hours. The aqueous layer was separated and the toluene layer washed with water. The aqueous washings and the aqueous layer were combined and residual toluene removed by distillation. Acetone (1684 kg) was added and the mixture cooled to 20° C. The sodium salt of (S)-enriched ibuprofen dihydrate (having an enantiomeric purity of 99.9%) separated, was collected by filtration and dried in vacuo. (Yield 143.5 kg).

Workup

  1. customThe aqueous layer was separated
  2. washthe toluene layer washed with water
  3. customresidual toluene removed by distillation
  4. additionAcetone (1684 kg) was added
  5. customseparated
  6. filtrationwas collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-89028e78ed534db184de502b0bf84df7
Source dataset
uspto-grants-1997_02
Patent number
US05599969

Reaction notes

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