Ethanol → Ethyl 2-(4-nitrophenyl)butanoate

HRID 1904019Notes

Reaction equation

HRID 1904019 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH2:14][CH3:15])[C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].S(=O)(=O)(O)O.[CH2:21](O)[CH3:22]>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH2:14][CH3:15])[C:11]([O:13][CH2:21][CH3:22])=[O:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 240472-(4-Nitrophenyl)butyric acid

Product 1

HCID 237528Ethyl 2-(4-nitrophenyl)butanoateYield 48%

Procedure

In 250 ml of ethanol was dissolved 16.71 g (0.08 mole) of 2-(4-nitrophenyl)-n-butyric acid and 15 ml of conc. sulfuric acid was then added and heated under reflux for 3.5 hours on an oil bath. After the ethanol was distilled off in vacuo, the residue was neutralized with saturated sodium bicarbonate solution and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated sodium chloride solution and dried over sodium sulfate. After the ethyl acetate was distilled off in vacuo, the residue was subjected to silica gel chromatography eluting with a mixture of benzene and n-hexane (1:1) to give 9.13 g (0.0385 mole, 48% yield) of ethyl 2-(4-nitrophenyl)-n-butyrate.

Workup

  1. additionwas then added
  2. temperatureheated
  3. temperatureunder reflux for 3.5 hours on an oil bath
  4. distillationAfter the ethanol was distilled off in vacuo
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. distillationAfter the ethyl acetate was distilled off in vacuo
  9. washeluting with a mixture of benzene and n-hexane (1:1)

Sources & evidence

ORD record
ord-73f17147e9ee400cac74000bfc31d0cf
Source dataset
uspto-grants-1984_03
Patent number
US04439448

Reaction notes

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