Selenium Dioxide → HCID 20608072, compound

HRID 2407165Notes

Reaction equation

HRID 2407165 reaction equation
[Se](=O)=[O:2].CC([C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9]([Cl:14])[CH:8]=1)=O.[O:15]1[CH2:20][CH2:19][O:18]CC1>>[Cl:13][C:11]1[CH:12]=[C:7]([C:19](=[O:18])[C:20]([OH:15])=[O:2])[CH:8]=[C:9]([Cl:14])[CH:10]=1

Participants

4

Reactant 3

HCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 27580583',5'-Dichloroacetophenone

Product 1

HCID 20608072HCID 20608072, compound

Conditions

Temperature
50 °C

Procedure

Selenium dioxide (30.0 g 270 mmol) was dissolved in dioxane (450 mL) and warmed to 50° C. 3,5-Dichloroacetophenone (30.0 g, 158 mmol) was added at at this temperature and the resulting mixture was refluxed for 4 h. After completion of the reaction, the mixture was filtered through celite and concentrated in vacuo. (3,5-Dichlorophenyl)(oxo)acetic acid was isolated and purified by column chromatography, eluting with ethyl acetate/hexane mixtures (28 g, 80%).

Workup

  1. temperaturethe resulting mixture was refluxed for 4 h
  2. customAfter completion of the reaction
  3. filtrationthe mixture was filtered through celite and
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e835a3dedb4a498796396aeceb7a695d
Source dataset
uspto-grants-2014_08
Patent number
US08809525B2

Reaction notes

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