Water → HCID 88719164, compound

HRID 1632243Notes

Reaction equation

HRID 1632243 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Se](=O)=[O:19].[OH2:21]>O1CCOCC1>[OH2:8].[CH:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([CH:16]=[O:19])=[O:17])=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1.[CH:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([CH:16]=[O:21])=[O:17])=[CH:11][CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 24007Selenium DioxideHCID 13340058HCID 13340058, compound

Product 1

HCID 88719164HCID 88719164, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 12.0 g of 4'-(cyclohexylmethoxy)acetophenone, 5.8 g of selenium dioxide, 1.4 ml of water and 70 ml of p-dioxane was refluxed with stirring at 120° C. for 18.5 hours, cooled and filtered through diatomaceous earth, washing with p-dioxane. The combined filtrate and wash was poured into 200 ml of water cooled to 8° C. The yellow solid was collected and dried. An 8.1 g portion of sodium bisulfite was dissolved in 500 ml of water. To this was added a solution of the above solid in a mixture of 300 ml of ethanol and 100 ml of p-dioxane. The resulting mixture was filtered and the filtrate stored at 0° C. for 48 hours. The resulting solid was collected, washed twice with water, p-dioxane and absolute ethanol and then dried. This solid was added to 535 ml of 0.5N hydrochloric acid and heated with stirring at 75° C. for 8 minutes and then cooled to 10° C. The solid was collected, dissolved in hot p-dioxane, filtered and 20 ml of water added to the filtrate. The filtrate was cooled to 0° C., giving the desired product as a white solid, m.p. 118°-121° C.

Workup

  1. temperaturewas refluxed
  2. temperaturecooled
  3. filtrationfiltered through diatomaceous earth
  4. washwashing with p-dioxane
  5. washThe combined filtrate and wash
  6. additionwas poured into 200 ml of water
  7. temperaturecooled to 8° C
  8. customThe yellow solid was collected
  9. customdried
  10. dissolutionAn 8.1 g portion of sodium bisulfite was dissolved in 500 ml of water
  11. additionTo this was added a solution of the above solid
  12. additionin a mixture of 300 ml of ethanol and 100 ml of p-dioxane
  13. filtrationThe resulting mixture was filtered
  14. waitthe filtrate stored at 0° C. for 48 hours
  15. customThe resulting solid was collected
  16. washwashed twice with water, p-dioxane and absolute ethanol
  17. customdried
  18. additionThis solid was added to 535 ml of 0.5N hydrochloric acid
  19. temperatureheated
  20. stirringwith stirring at 75° C. for 8 minutes
  21. temperaturecooled to 10° C
  22. customThe solid was collected
  23. dissolutiondissolved in hot p-dioxane
  24. filtrationfiltered
  25. addition20 ml of water added to the filtrate
  26. temperatureThe filtrate was cooled to 0° C.

Sources & evidence

ORD record
ord-4f27a9a52f68404a8feb991eb2a5f227
Source dataset
uspto-grants-1984_10
Patent number
US04474809

Reaction notes

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