Sulfuric Acid → Ibuprofen, (+-)-

HRID 1449227Notes

Reaction equation

HRID 1449227 reaction equation
[O-: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].[Na+].S(=O)(=O)(O)O.[Cl-].[Na+]>>[OH: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

4

Reactant 3

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 5338317Ibuprofen, Sodium Salt

Product 1

HCID 3672Ibuprofen, (+-)-Yield 93.2%

Procedure

The aqueous basic fraction containing sodium ibuprofen salt was acidified with 6N sulfuric acid, sodium chloride was added, and then extracted twice with Skellysolve B to take up the ibuprofen acid product therein. The Skellysolve B phase was dried over sodium sulfate and evaporated to leave as residue 867.7 mg. (93.2 percent yield) of ibuprofen which was 99.9 percent pure by gas liquid chromatographic (GLC) analysis.

Workup

  1. additionwas added
  2. extractionextracted twice with Skellysolve B
  3. dry with materialThe Skellysolve B phase was dried over sodium sulfate
  4. customevaporated
  5. customto leave as residue 867.7 mg

Sources & evidence

ORD record
ord-9fb0f63a25da4ea98b6394c83ae0b917
Source dataset
uspto-grants-1980_02
Patent number
US04189596

Reaction notes

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