Methanol → Ibuprofen, (+-)-

HRID 1719816Notes

Reaction equation

HRID 1719816 reaction equation
CS(O[CH:6](C)[C:7]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:14][CH:13]=1)(OC)OC)(=O)=O.[C:23](=[O:26])(O)[O-:24].[Na+].CO>O>[CH2:18]([C:15]1[CH:14]=[CH:13][C:12]([CH:7]([CH3:6])[C:23]([OH:24])=[O:26])=[CH:17][CH:16]=1)[CH:19]([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 12756316HCID 12756316, compound

Product 1

HCID 3672Ibuprofen, (+-)-Yield 72.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 17 g of 1-(4-isobutylphenyl)-1,1-dimethoxyprop-2-yl methanesulfonate from Example 21, 16.5 g of sodium bicarbonate, 170 ml of methanol and 135 ml of water is heated to 67°-70° C. and held at reflux for 23 hours. Then the methanol is distilled from the reaction mixture and the aqueous phase remaining is extracted with 150 ml of methylene chloride. The aqueous phase is acidified with concentrated hydrochloric acid and extracted with 150 ml of methylene chloride. The organic phase is dried over magnesium sulfate, and the solvent evaporated to yield 7.67 g of 2-(4-isobutylphenyl)propionic acid (melting point: 73°-75° C.).

Workup

  1. temperatureis heated to 67°-70° C.
  2. temperatureat reflux for 23 hours
  3. distillationThen the methanol is distilled from the reaction mixture
  4. extractionthe aqueous phase remaining is extracted with 150 ml of methylene chloride
  5. extractionextracted with 150 ml of methylene chloride
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-d577de9574ce42518b7690e141401f70
Source dataset
uspto-grants-1985_09
Patent number
US04542237

Reaction notes

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