Methanol → Ibuprofen, (+-)-

HRID 652289Notes

Reaction equation

HRID 652289 reaction equation
Br[CH:2]([C:4]1([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:11][CH:10]=2)OCCO1)C.ClC1C=CC=CC=1.[OH-:26].[Na+].[CH3:28][OH:29]>[O-2].[Zn+2]>[CH2:15]([C:12]1[CH:11]=[CH:10][C:9]([CH:4]([CH3:2])[C:28]([OH:29])=[O:26])=[CH:14][CH:13]=1)[CH:16]([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 7964ChlorobenzeneHCID 14798Sodium HydroxideHCID 131703952-(1-Bromoethyl)-2-[4-(2-methylpropyl)phenyl]-1,3-dioxolane

Product 1

HCID 3672Ibuprofen, (+-)-Yield 99%

Reagents, catalysts & solvents 1

HCID 3007857Zinc OxideCatalyst

Procedure

In a reactor, 32 g (0.10 mol) of 2-(1'-bromoethyl)-2-(4'-isobutylphenyl)-1,3-dioxolane, 0,81 g (0.01 mol) of zinc oxide, and 40 ml of monochlorobenzene were heated at 140° C. for two hours. The resultant reaction mixture was filtered to recover the catalyst (93%) and then distilled to expel the monochlorobenzene. Then, the residue was subjected to hydrolysis by following the procedure of Example 10 (150 ml of methanol and 400 ml of 50% NaOH aqueous solution). Consequently, there was obtained 2-(4'-isobutylphenyl)-propionic acid in a yield of 99%. When the same reaction was repeated by using the recovered zinc oxide as the catalyst, there was obtained 2-(4'-isobutylphenyl)-propionic acid in a yield of 95%.

Workup

  1. customThe resultant reaction mixture
  2. filtrationwas filtered
  3. customto recover the catalyst (93%)
  4. distillationdistilled
  5. customThen, the residue was subjected to hydrolysis

Sources & evidence

ORD record
ord-f5c36e5415cb4ddcafbab3ea7947b5b4
Source dataset
uspto-grants-1987_06
Patent number
US04670586

Reaction notes

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