Ethanol → Ethyl alpha-oxobenzenebutanoate

HRID 1632369Notes

Reaction equation

HRID 1632369 reaction equation
[O:1]=[C:2]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([OH:5])=[O:4].S(=O)(=O)(O)O.[CH2:19](O)[CH3:20]>>[O:1]=[C:2]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH2:19][CH3:20])=[O:4]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 697322-Oxo-4-phenylbutyric acid

Product 1

HCID 562087Ethyl alpha-oxobenzenebutanoate

Procedure

2-Oxo-4-phenylbutyric acid (130 g) is added to a mixture of 650 ml of ethanol and 13 ml of concentrated sulfuric acid, and the whole mixture is refluxed for 5 hours. The reaction mixture is concentrated to approximately half the original volume, and then diluted with 500 ml of water. The resulting oil is collected and, the aqueous layer is extracted with ethyl acetate. The extract and the oil are combined and dried, and the solvent is distilled off under reduced pressure. The residue is distilled under reduced pressure to give 113 g of ethyl 2-oxo-4-phenylbutyrate as a colorless oil boiling at 135°-141° C./3 mmHg.

Workup

  1. temperaturethe whole mixture is refluxed for 5 hours
  2. concentrationThe reaction mixture is concentrated to approximately half the original volume
  3. additiondiluted with 500 ml of water
  4. customThe resulting oil is collected
  5. extractionthe aqueous layer is extracted with ethyl acetate
  6. extractionThe extract
  7. customdried
  8. distillationthe solvent is distilled off under reduced pressure
  9. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-9f92bc430a5540c5aa0f22ebda7d36da
Source dataset
uspto-grants-1984_10
Patent number
US04474692

Reaction notes

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