Water → Ibuprofen, (+-)-

HRID 1605217Notes

Reaction equation

HRID 1605217 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:14])[CH:12]=[O:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].S(=O)(=O)(O)[OH:16].O.C(Cl)Cl>CC(C)=O.[O-2].[O-2].[O-2].[Cr+6]>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:14])[C:12]([OH:16])=[O:13])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 962Water2×HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 595156Ibuprofenal

Product 1

HCID 3672Ibuprofen, (+-)-

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 180AcetoneSolvent

Conditions

Temperature
-25 °C

Procedure

190 mg of α-(p-isobutylphenyl)-propionaldehyd are dissolved in 15 ml of acetone, and the solution cooled to -25° C is added to 220 ml of a solution containing 30 g chromiumtrioxide, 25 ml of concentrated sulfuric acid and water per 100 ml. The whole stirred for one hour at -25° C, the temperature was allowed to rise to about 0° C while stirring and then the reaction mixture was poured into a mixture of 20 ml water and 60 ml of methylene chloride. The two phases are separated and the watery phase washed two times with 30 ml of methylene chloride each time. The organic layers are dryed over magnesiumsulfat and evaporated. These were obtained 157 mg of α-(p-isobutylphenyl)-propionic acid, which melted after recrystallisation from few hexane at 74°-75.5°. This compound is known as "IBUPROFEN" and is used as antiinflammatory agent (cf. Brit. Pat. No. 971,700 and French Pat. No. 1,545,270).

Workup

  1. customto rise to about 0° C
  2. stirringwhile stirring
  3. customThe two phases are separated
  4. washthe watery phase washed two times with 30 ml of methylene chloride each time
  5. customevaporated

Sources & evidence

ORD record
ord-f9ee8bacf6f24432a82a4d9d4cb51b70
Source dataset
uspto-grants-1976_04
Patent number
US03950327

Reaction notes

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