Sodium Hydroxide → Ibuprofen, Sodium Salt

HRID 1731901Notes

Reaction equation

HRID 1731901 reaction equation
[OH-].[Na+:2].[OH:3][C:4]([CH:6]([C:8]1[CH:17]=[CH:16][C:11]([CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:10][CH:9]=1)[CH3:7])=[O:5].[Na]>O>[O-:5][C:4]([CH:6]([C:8]1[CH:9]=[CH:10][C:11]([CH2:12][CH:13]([CH3:14])[CH3:15])=[CH:16][CH:17]=1)[CH3:7])=[O:3].[Na+:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 4505253531121-93-4

Product 1

HCID 5338317Ibuprofen, Sodium Salt

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
95 °C

Procedure

The chloroester solution prepared in (c) was heated to reflux at 95°-100° C. and 13 kg of 50% sodium hydroxide in water was added over twenty minutes. The mixture was refluxed for forty minutes at 95±5° C. GLC analysis of an aliquot indicated complete reaction. 6.4 liters of water were slowly added to the mixture, keeping the temperature about 75° C. After water addition was complete, the mixture was cooled to 70° C. and was seeded with 30 g of good quality sodium ibuprofen. The resulting slurry was cooled to 0° C. over two hours. The slurry was stirred at 0° C. for thirty minutes and filtered. The sodium ibuprofen cake was washed wih 60 kg of heptane and dried.

Workup

  1. temperaturewas heated
  2. temperatureto reflux at 95°-100° C.
  3. customreaction
  4. customthe temperature about 75° C
  5. temperaturethe mixture was cooled to 70° C.
  6. temperatureThe resulting slurry was cooled to 0° C. over two hours
  7. filtrationfiltered
  8. washThe sodium ibuprofen cake was washed wih 60 kg of heptane
  9. customdried

Sources & evidence

ORD record
ord-e252033bf9fb4d2e8e242cca3d0ce01d
Source dataset
uspto-grants-1986_11
Patent number
US04623736

Reaction notes

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