Ethanol → Ethyl 2-nitrophenylacetate

HRID 1372730Notes

Reaction equation

HRID 1372730 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=[O:12])([O-:3])=[O:2].OS(O)(=O)=O.[CH2:19](O)[CH3:20]>C(OCC)(=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([O:13][CH2:19][CH3:20])=[O:12])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 77337(2-Nitrophenyl)acetic acid

Product 1

HCID 595882Ethyl 2-nitrophenylacetateYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In ethanol (250 ml) was dissolved (2-nitrophenyl)acetic acid (18.5 g, 0.102 mmol), and to the resulting solution was added concentrated H2SO4 (0.1 ml). The mixture was heated under reflux for 24 hours. The reaction mixture was cooled to room temperature and then, diluted with ethyl acetate. The diluted solution was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, whereby ethyl (2-nitrophenyl)acetate (17.4 g, 82%) was obtained as a colorless solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. washThe diluted solution was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent

Sources & evidence

ORD record
ord-c92c2eb2603d4055935d044c1b6c7301
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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