Hydrogen Peroxide → (2S)-2-(4-methoxyphenyl)propanoic acid

HRID 1755810Notes

Reaction equation

HRID 1755810 reaction equation
C([C@H]1COC(=O)N1[C:14](=[O:25])[C@H:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[CH3:16])C1C=CC=CC=1.[O-:26]O.[Li+].O[Li].O.OO>C1COCC1.O.C(OCC)(=O)C>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([C@H:15]([CH3:16])[C:14]([OH:25])=[O:26])=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 168937Lithium hydroxide, monohydrateHCID 23689669Lithium peroxide (Li(O2H))HCID 57187912(2S, 4S)-4-benzyl-3-(1-oxo-2-(4-methoxy-phenyl)-propyl)-2-oxazolidinone

Product 1

HCID 12398859(2S)-2-(4-methoxyphenyl)propanoic acidYield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mechanically stirred solution of the above amide (27) (56.2 g) in THF (750 mL) and H2O (250 mL) at 0° C. was added a solution of lithium hydroperoxide prepared by adding a solution of LiOH.H2O (10.4 g) in H2O (250 mL) to 30% H2O2 (84 mL). After stirring for 1 h at 0° C. the excess peroxide was destroyed by the slow addition of a solution of Na2SO3 (103 g) in H2O (500 mL) (exothermic!). After removing most of the THF by evaporation the remaining solution was washed with CH2Cl2 twice to remove recoverable (S)-4-benzyl-2-oxazolidinone, acidified to pH ~2 with 3N HCl and extracted twice with ethyl acetate to isolate the product. The ethyl acetate phases were combined, washed with saturated NaCl, dried over MgSO4 and evaporated to give TLC pure product, (28) (29.87 g, 100%). TLC Rf 0.49 (95:4:1 CHCl3 :MeOH:HOAc) Rf 0.33 streaks (98:2 CHCl3 :MeOH); 1H NMR (CDCl3)δ1.5(3H, d, J=7 HZ), 2.25 (2H, br s), 2.78 (3H, s), 4.08 (1H, q), 7.15 (4H, q).

Workup

  1. customprepared
  2. customwas destroyed by the slow addition of a solution of Na2SO3 (103 g) in H2O (500 mL) (exothermic!)
  3. customAfter removing most of the THF by evaporation the remaining solution
  4. washwas washed with CH2Cl2 twice
  5. customto remove recoverable (S)-4-benzyl-2-oxazolidinone
  6. extractionextracted twice with ethyl acetate
  7. customto isolate the product
  8. washwashed with saturated NaCl
  9. dry with materialdried over MgSO4
  10. customevaporated

Sources & evidence

ORD record
ord-11b9354abfe746228432d53eeb07705a
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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