Ethanol → Benzeneacetic acid, 2,4-dinitro-, ethyl ester

HRID 1655838Notes

Reaction equation

HRID 1655838 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][C:14]([OH:16])=[O:15])([O-:3])=[O:2].S(=O)(=O)(O)O.[CH2:22](O)[CH3:23]>>[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][C:14]([O:16][CH2:22][CH3:23])=[O:15])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 2215132,4-Dinitrophenylacetic acid

Product 1

HCID 106546Benzeneacetic acid, 2,4-dinitro-, ethyl ester

Procedure

A mixture containing 2,4-dinitrophenylacetic acid (100 g, 0.442 mol), concentrated sulfuric acid (1.5 mL) and ethanol (700 mL) is heated at reflux for 61/2 hours, cooled to room temperature and filtered. The filtrate is concentrated in vacuo to a volume of 200 mL then diluted with water. The pH of the aqueous mixture is adjusted to about a with solid sodium hydrogen carbonate and extracted with ether. The combined organic extracts are washed with water, dried over anhydrous sodium sulfate, decolorized with charcoal and concentrated in vacuo to obtain the title compound as a yellow oil (102.4 g).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 61/2 hours
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated in vacuo to a volume of 200 mL
  5. additionthen diluted with water
  6. extractionextracted with ether
  7. washThe combined organic extracts are washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-791e0595b643437cb494aec6381e92f4
Source dataset
uspto-grants-1993_10
Patent number
US05252536

Reaction notes

Loading…