Water → HCID 20444150, compound

HRID 1632244Notes

Reaction equation

HRID 1632244 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.O.[Se](=O)=[O:22]>O1CCOCC1>[OH2:2].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([C:17](=[O:19])[CH:18]=[O:22])=[CH:15][CH:16]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24007Selenium DioxideHCID 10377701Ethanone, 1-[4-[(4-methoxyphenyl)methoxy]phenyl]-

Product 1

HCID 20444150HCID 20444150, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 10.0 g portion of 1-[4-[(4-methoxyphenyl)-methoxy]phenyl]ethanone was dissolved in 50 ml of hot p-dioxane. A 2.0 ml portion of water and 4.4 g of selenium dioxide were added and the mixture was stirred at reflux for 67 hours, then cooled and filtered through diatomaceous earth. The filtrate was poured into 300 ml of water and the solid collected. This solid was extracted with eight 100 ml portions of ethyl acetate. The extracts were combined, washed with water, dried and evaporated. The residue was dissolved in 100 ml of boiling toluene, treated with charcoal and filtered through diatomaceous earth. The filtrate was treated with 200 ml. of hexane, giving the desired product as a pale yellow solid, m.p. 127°-138° C.

Workup

  1. temperatureat reflux for 67 hours
  2. temperaturecooled
  3. filtrationfiltered through diatomaceous earth
  4. additionThe filtrate was poured into 300 ml of water
  5. customthe solid collected
  6. extractionThis solid was extracted with eight 100 ml portions of ethyl acetate
  7. washwashed with water
  8. customdried
  9. customevaporated
  10. dissolutionThe residue was dissolved in 100 ml of boiling toluene
  11. additiontreated with charcoal
  12. filtrationfiltered through diatomaceous earth
  13. additionThe filtrate was treated with 200 ml

Sources & evidence

ORD record
ord-020bdd08cd31490a83f4e9284a26f9ba
Source dataset
uspto-grants-1984_10
Patent number
US04474809

Reaction notes

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