Hydrochloric Acid → Ibuprofen, (+-)-

HRID 1731420Notes

Reaction equation

HRID 1731420 reaction equation
[CH3:1][CH:2]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:11][CH:10]=1)[C:3](=[O:8])C(OC)=O.[OH:19]O.Cl>[OH-].[Na+]>[CH2:15]([C:12]1[CH:13]=[CH:14][C:9]([CH:2]([CH3:1])[C:3]([OH:8])=[O:19])=[CH:10][CH:11]=1)[CH:16]([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 12225939HCID 12225939, compound

Product 1

HCID 3672Ibuprofen, (+-)-Yield 79%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 3-methyl-3-(4-isobutylphenyl)pyruvate (1.19 g, 4.8 mmol) was dissolved in a 1N sodium hydroxide aqueous solution (15 ml), and a 35% hydrogen peroxide aqueous solution (5.0 ml) was dropwise added under cooling (0° C.) and stirring. The temperature of the mixture was returned to room temperature, and the mixture was stirred overnight. Then, mixture was acidified with hydrochloric acid and extracted with ether, whereby 2-(4-isobutylphenyl)propionic acid (0.78 g, yield: 79%) was obtained.

Workup

  1. customwas returned to room temperature
  2. stirringthe mixture was stirred overnight
  3. extractionextracted with ether

Sources & evidence

ORD record
ord-76f68280b94944989760d3f03860b8e4
Source dataset
uspto-grants-1986_11
Patent number
US04621150

Reaction notes

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