Ethylene Glycol → Ibuprofen, (+-)-

HRID 652290Notes

Reaction equation

HRID 652290 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.[OH-:19].[Na+].Cl.[CH2:22]([OH:25])CO>[O-2].[Zn+2]>[CH2:15]([C:12]1[CH:11]=[CH:10][C:9]([CH:4]([CH3:2])[C:22]([OH:25])=[O:19])=[CH:14][CH:13]=1)[CH:16]([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131703952-(1-Bromoethyl)-2-[4-(2-methylpropyl)phenyl]-1,3-dioxolane

Product 1

HCID 3672Ibuprofen, (+-)-Yield 83%

Reagents, catalysts & solvents 1

HCID 3007857Zinc OxideCatalyst

Procedure

In a reactor, 3.2 g (0.01 mol) of 2-(1'-bromoethyl)-2-(4'-isobutylphenyl)-1,3-dioxolane, 0.081 g (0.001 mol) of zinc oxide, and 15 ml of ethylene glycol were refluxed under application of heat for four hours. The resultant reaction mixture and 30 ml of an aqueous solution containing sodium hydroxide in a concentration of 50% by weight added thereto were refluxed under application of heat for four hours. The resultant aqueous solution was acidified with concentrated hydrochloric acid and then extracted twice, each from 40 ml of toluene. Then, the extract was distilled to expel the toluene. Consequently, there was obtained 1.7 g (0.008 mol) of 2-(4'-isobutylphenyl)-propionic acid. This product represented a yield of 83% and showed a melting point of 76° to 77° C.

Workup

  1. temperatureof heat for four hours
  2. additionadded
  3. temperaturethereto were refluxed under application
  4. temperatureof heat for four hours
  5. extractionextracted twice
  6. distillationThen, the extract was distilled

Sources & evidence

ORD record
ord-908b1b13744a4bd198f40194532fdbd4
Source dataset
uspto-grants-1987_06
Patent number
US04670586

Reaction notes

Loading…