4'-Hydroxyacetophenone → (4-Hydroxyphenyl)(oxo)acetaldehyde--water (1/1)

HRID 1981468Notes

Reaction equation

HRID 1981468 reaction equation
[Se](=O)=[O:2].[O:4]1[CH2:9][CH2:8][O:7]CC1.CC([C:13]1[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=1)=O>O>[OH2:2].[OH:19][C:16]1[CH:17]=[CH:18][C:13]([C:9]([CH:8]=[O:7])=[O:4])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 24007Selenium DioxideHCID 312751,4-Dioxane

Product 1

HCID 23318533(4-Hydroxyphenyl)(oxo)acetaldehyde--water (1/1)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Selenium dioxide (11.1 g, 0.1 mol) was added to a mixed solution of p-dioxane (60 cc) and water (2 cc) and dissolved therein on heating at 60° C., followed by adding 4-hydroxyacetophenone (13.6 g, 0.1 mol) all at once, reacting the mixture on heating under reflux for 4 hours, filtering off an inorganic material deposited after completion of the reaction, distilling off p-dioxane from the filtrate, adding water (80 cc) to the resulting red-brown oily material, heating the mixture with stirring at 80° C. for 2 hours, allowing the reaction liquid to cool down to room temperature after completion of the reaction, and filtering off and drying deposited crystals to obtain the objective product (10.7 g). M.p.: 109°~111° C.

Workup

  1. dissolutiondissolved
  2. temperatureon heating
  3. temperatureunder reflux for 4 hours
  4. filtrationfiltering off an inorganic material
  5. customafter completion of the reaction
  6. distillationdistilling off p-dioxane from the filtrate
  7. additionadding water (80 cc) to the resulting red-brown oily material
  8. temperatureheating the mixture
  9. customthe reaction liquid
  10. temperatureto cool down to room temperature
  11. customafter completion of the reaction
  12. filtrationfiltering off
  13. customdrying

Sources & evidence

ORD record
ord-138bb18888c64cb2ae590e0c2526ff88
Source dataset
uspto-grants-1986_06
Patent number
US04592857

Reaction notes

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