Acetic Acid → 2,4-Dihydroxy-4b,6,7,8,8a,10-hexahydrophenanthren-9(5H)-one

HRID 258636

Reaktionsgleichung

Reaktionsgleichung von HRID 258636
[OH-].[K+].[C:3]1([CH:11]=[C:9]([OH:10])[CH:8]=[C:6]([OH:7])[CH:5]=1)O.[C:12]([C:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]=1)(=[O:14])[CH3:13].C(O)(=O)C>COCCO.C(OCC)(=O)C>[OH:7][C:6]1[CH:8]=[C:9]([OH:10])[C:11]2[CH:20]3[CH:15]([CH2:16][CH2:17][CH2:18][CH2:19]3)[C:12](=[O:14])[CH2:13][C:3]=2[CH:5]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 359PhloroglucinolHCID 136121-AcetylcyclohexeneHCID 14797Potassium Hydroxide

Produkt 1

HCID 203227742,4-Dihydroxy-4b,6,7,8,8a,10-hexahydrophenanthren-9(5H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 80192-MethoxyethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

To a flask equipped with a stirrer, dropping funnel, condenser and gas inlet tube maintained under a nitrogen atmosphere, there is added 50 g. (0.89) moles of potassium hydroxide in one liter of 2-methoxyethanol. Stirring is initiated and 100 g. (0.79 mole) of anhydrous phloroglucinol is added in three portions, followed by the addition of 100 g. (0.80 mole) of 1-acetyl-cyclohexene while maintaining the temperature at 50° C. The resulting solution is refluxed at 140° C. for 4 hours. After cooling there is then added gradually 53.6 g. of acetic acid while obtaining a pH of approximately 7. The solvent is then removed in vacuo, and the residue is further heated in an oil bath at 70° C., to obtain a viscous residue. The resulting residue is dissolved in ethyl acetate and water washed twice with water, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to obtain a brown solid. The resulting solid is recrystallized from ethyl acetate/cyclohexane to give 2,4-dihydroxy-4b,5,6,7,8,8a,9,10-octahydro-9-oxo-phenanthrene; m.p. 220°-223° C.

Aufarbeitung

  1. customTo a flask equipped with a stirrer
  2. temperaturemaintained under a nitrogen atmosphere
  3. additionthere is added 50 g
  4. additionfollowed by the addition of 100 g
  5. temperatureAfter cooling there
  6. additionis then added gradually 53.6 g
  7. customThe solvent is then removed in vacuo
  8. temperaturethe residue is further heated in an oil bath at 70° C.
  9. customto obtain a viscous residue
  10. washwater washed twice with water
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. customevaporated in vacuo
  14. customto obtain a brown solid
  15. customThe resulting solid is recrystallized from ethyl acetate/cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-62fd1dc90f0243119c29b2b0a50756aa
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04034045

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