Water → 2-Benzyl-3-(p-nitrophenyl)propionic acid

HRID 1440398Notes

Reaction equation

HRID 1440398 reaction equation
[CH2:1]([C:8]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)(C(OCC)=O)[C:9]([O:11]CC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].O>C(O)C>[CH2:1]([CH:8]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=1)[C:9]([OH:11])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 53932722Diethyl benzyl-4-nitrobenzylmalonate

Product 1

HCID 218482572-Benzyl-3-(p-nitrophenyl)propionic acidYield 59.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of diethyl benzyl-4-nitrobenzylmalonate (24 g), KOH (14 g) and water (100 ml)-ethanol (150 ml) was stirred at 90°-100° C. for 7 hours. The reaction mixture was concentrated under reduced pressure and the residue was acidified with 1N HCl and extracted with ethylacetate. The ethyl acetate layer was washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residue was dissolved in pyridine (100 ml) and the solution was stirred at 90° C. for 16 hours. The organic solvent was evaporated off and the residue was acidified with 1N HCl and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried (MgSO4) and concentrated under reduced pressure. The residual oil was purified by column chromatography on silica gel. Elution with ethyl acetate-hexane (1:3, v/v) gave 2-benzyl-3-(p-nitrophenyl)propionic acid (10.5 g, 59%) as crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with ethylacetate
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in pyridine (100 ml)
  7. stirringthe solution was stirred at 90° C. for 16 hours
  8. customThe organic solvent was evaporated off
  9. extractionextracted with ethyl acetate
  10. washThe ethyl acetate layer was washed with brine
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated under reduced pressure
  13. customThe residual oil was purified by column chromatography on silica gel
  14. washElution with ethyl acetate-hexane (1:3

Sources & evidence

ORD record
ord-d788c5fc886f48e690dce0f951263dfa
Source dataset
uspto-grants-1996_03
Patent number
US05498728

Reaction notes

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