Hydrogen Peroxide → 4-{[1,1'-Biphenyl]-4-yl}butanoic acid

HRID 1941308Notes

Reaction equation

HRID 1941308 reaction equation
OO.[Li+].[OH-:4].[O:5]1[CH2:9][CH2:8]NC1=O.CCO[CH2:14][CH3:15].[CH2:16]1[CH2:20]O[CH2:18][CH2:17]1>>[C:16]1([C:15]2[CH:14]=[CH:18][CH:17]=[CH:16][CH:20]=2)[CH:20]=[CH:20][C:16]([CH2:17][CH2:18][CH2:8][C:9]([OH:5])=[O:4])=[CH:18][CH:17]=1

Participants

6

Reactant 5

HCID 784Hydrogen PeroxideHCID 3283Diethyl EtherHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 739492-Oxazolidinone

Product 1

HCID 111392304-{[1,1'-Biphenyl]-4-yl}butanoic acid

Procedure

To a solution of the above (5.71 g, 10.8 mmol) in 67 ml THF/17 ml water cooled to 0° C. was added a mixture 8.8 ml of 30% H2O2 43.3 mmol of LiOH. The solution was evaporated after 1.5 h, and the resulting material acidified with 10% citric acid. The organic material was extracted with ethyl acetate, washed with water and brine and dried over MgSO4. Filtration and removal of solvent gave a slurry containing the oxazolidinone and crude acid. Addition of ether and a seed crystal of S-4-(phenylmethyl)oxazolidinone followed by cooling to -20, gave a solid precipitate which was removed by filtration. The product acid was further purified by making a dicylohexylamine salt and recrystalizing from ether. The acid was then free based using 5% KHSO4 to give the acid as a crystailne product that could be used without further purification in the next step.

Workup

  1. customThe solution was evaporated after 1.5 h
  2. extractionThe organic material was extracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and removal of solvent
  6. customgave a slurry
  7. temperatureby cooling to -20
  8. customgave a solid precipitate which
  9. customwas removed by filtration
  10. customThe product acid was further purified
  11. customrecrystalizing from ether
  12. customto give the acid as a crystailne product that
  13. customcould be used without further purification in the next step

Sources & evidence

ORD record
ord-4fddb1cd3e9c4336a115af9d16b83996
Source dataset
uspto-grants-1997_12
Patent number
US05703092

Reaction notes

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