Water → 4-(2,4-Dihydroxyphenyl)cyclohexanone

HRID 346818

Reaktionsgleichung

Reaktionsgleichung von HRID 346818
O1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=3[OH:18])[CH2:7][CH2:6]2)[O:4]CC1.O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O>[OH:18][C:12]1[CH:13]=[C:14]([OH:17])[CH:15]=[CH:16][C:11]=1[CH:8]1[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 99212574-(1,4-Dioxaspiro[4.5]dec-8-yl)-1,3-benzenediol

Produkt 1

HCID 99424894-(2,4-Dihydroxyphenyl)cyclohexanoneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

A flask equipped with magnetic stirrer was charged with 4-(1,4-dioxaspiro[4.5]dec-8-yl)-1,3-benzenediol (11.3 g, 45.2 mmol), acetone (250 ml) and water (50 ml). To the stirred solution was added pyridinium p-toluenesulfonate (1.14 g, e.52 mmol) in one portion and the reaction mixture as then heated under reflux for 8 hr. After allowing the reaction mixture to cool to room temperature, most of the acetone was removed in vacuo and the remaining mixture was partitioned between ethyl acetate (200 ml) and water (50 ml). The aqueous layer extracted with ethyl acetate (3 ×50 ml) and the combined organic layers were washed with brine (30 ml), dried (MgSO4), filtered and concentrated under reduced pressure to afford an off-white powder. After washing the powder with dichloromethane (100 ml) and removal of excess solvent under reduced pressure, the title compound (9.30 g, 100%) was obtained as an off-white powder. M/z (ES+) 207 (M+H+).

Aufarbeitung

  1. customA flask equipped with magnetic stirrer
  2. temperaturethe reaction mixture as then heated
  3. temperatureunder reflux for 8 hr
  4. customwas removed in vacuo
  5. customthe remaining mixture was partitioned between ethyl acetate (200 ml) and water (50 ml)
  6. extractionThe aqueous layer extracted with ethyl acetate (3 ×50 ml)
  7. washthe combined organic layers were washed with brine (30 ml)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto afford an off-white powder
  12. washAfter washing the powder
  13. customwith dichloromethane (100 ml) and removal of excess solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-99894fcc20fa47169198ab69853e9e3a
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173052B2

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