Hydrochloric Acid → 4-(2,4-Dihydroxyphenyl)cyclohexanone

HRID 585685

Reaktionsgleichung

Reaktionsgleichung von HRID 585685
COC[O:4][C:5]1[CH:10]=[C:9]([O:11]COC)[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:24][CH2:23][C:18]2(OCC[O:19]2)[CH2:17][CH2:16]1.Cl>CO>[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:16][CH2:17][C:18](=[O:19])[CH2:23][CH2:24]1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 121351698-[2,4-Bis(methoxymethoxy)phenyl]-1,4-dioxaspiro[4.5]decane

Produkt 1

HCID 99424894-(2,4-Dihydroxyphenyl)cyclohexanoneAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A round bottomed flask equipped with magnetic stirrer was loaded 8-[2,4-bis(methoxymethoxy)phenyl]-1,4-dioxaspiro[4.5]decane (1.30 g, 3.9 mmol) and methanol (15 ml). To the resulting stirred solution was added aqueous HCl (15 ml, 1M) in one portion. After stirring for one hr at room temperature the acid was quenched by adding saturated aqueous sodium bicarbonate solution (10 ml). After stirring vigorously for 10 min, the reaction mixture was transferred to a separating funnel and the phases separated and the aqueous phase was extracted with ethyl acetate (3×20 ml). The combined organic phases were washed with brine and the solvent evaporated. To the slightly wet crude product was added methanol (30 ml) and acidic ion exchange resin (4 g). The resulting mixture was heated under reflux, with stirring, for 5 hr. Filtering through a plug of Celite, washing with ethyl acetate, followed by removal of solvent in vacuo afforded an orange oil. Purification by flash column chromatography, (SiO2, ethyl acetate/petroleum ether, 1:1, v/v) furnished the title compound as a white powder (0.54 g, 68%). m/z (ES−) 411 (2M−1); δH (CD3OD) 1.94 (2H, ddd), 2.16-2.23 (2H, m), 2.41 (2H, dt), 2.62 (1H, t), 2.63 (1H, t), 6.24 (1H, dd), 6.31 (1H, d), 6.92 (1H, d).

Aufarbeitung

  1. customA round bottomed flask equipped with magnetic stirrer
  2. stirringAfter stirring for one hr at room temperature the acid
  3. customwas quenched
  4. additionby adding saturated aqueous sodium bicarbonate solution (10 ml)
  5. stirringAfter stirring vigorously for 10 min
  6. customthe reaction mixture was transferred to a separating funnel
  7. customthe phases separated
  8. extractionthe aqueous phase was extracted with ethyl acetate (3×20 ml)
  9. washThe combined organic phases were washed with brine
  10. customthe solvent evaporated
  11. additionTo the slightly wet crude product was added methanol (30 ml) and acidic ion exchange resin (4 g)
  12. temperatureThe resulting mixture was heated
  13. temperatureunder reflux
  14. stirringwith stirring, for 5 hr
  15. filtrationFiltering through a plug of Celite
  16. washwashing with ethyl acetate
  17. customfollowed by removal of solvent in vacuo
  18. customafforded an orange oil
  19. customPurification by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fcd04468a40f4e9abc134d51f3acbf4e
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06933319B2

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