2-(4-Nitrophenyl)propionic acid → Ethyl 2-(4-nitrophenyl)propionate

HRID 2413909Notes

Reaction equation

HRID 2413909 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:14])[C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[CH2:16](O)[CH3:17]>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH3:14])[C:11]([O:13][CH2:16][CH3:17])=[O:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 892442-(4-Nitrophenyl)propionic acidHCID 21887872Ethanol hydrochloride

Product 1

HCID 3016550Ethyl 2-(4-nitrophenyl)propionate

Procedure

23.3 g of the crude 2-(4-nitrophenyl)propionic acid was dissolved in 100 ml of 22% hydrochloric acid-ethanol solution, and the solution was refluxed on an oil bath for two hours. After ethanol was distilled off under reduced pressure, the residue was neutralized with a saturated solution of sodium bicarbonate and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated solution of sodium chloride and dried over anhydrous sodium sulfate. After distilling off ethyl acetate under reduced pressure, the residue was subjected to silica gel chromatography with chloroform solvent to give 55 g of ethyl 2-(4-nitrophenyl)propionate.

Workup

  1. temperaturethe solution was refluxed on an oil bath for two hours
  2. distillationAfter ethanol was distilled off under reduced pressure
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with a saturated solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationAfter distilling off ethyl acetate under reduced pressure

Sources & evidence

ORD record
ord-3b420cf524194de5b7a12cde94dbb81b
Source dataset
uspto-grants-1988_01
Patent number
US04720506

Reaction notes

Loading…