Sodium Bicarbonate → 3-(10-Hydroxydecyl)-4-methyl-2-cyclohexene-1-one

HRID 1976747Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1976747
C1CO[C:3]2([CH2:8][CH2:7][CH:6]([CH3:9])[C:5]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])(S(C3C=CC=CC=3)(=O)=O)[CH2:4]2)[O:2]1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.CC(C)=O>[OH:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:5]1[CH:6]([CH3:9])[CH2:7][CH2:8][C:3](=[O:2])[CH:4]=1

Komponenten

5

Edukt 2

HCID 516892Sodium BicarbonateHCID 219991391,1-(Ethylenedioxy)-3-(10-hydroxydecyl)-4-methyl-3-(phenylsulfonyl)-cyclohexane

Produkt 1

HCID 106354973-(10-Hydroxydecyl)-4-methyl-2-cyclohexene-1-oneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Paratoluenesulfonic acid (20 m) was added to a solution of 235 mg of 1,1-(ethylenedioxy)-3-(10-hydroxydecyl)-4-methyl-3-(phenylsulfonyl)-cyclohexane in 20 ml of chloroform and 4 ml of acetone. The resulting mixture was reacted at 50° C. for 24 hours. To the reaction mixture were added 10 ml of a saturated aqueous solution of sodium bicarbonate, followed by extraction with dichloromethane. The organic layer was washed with saturated saline and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column while using hexane-ethyl acetate, whereby 3-(10-hydroxydecyl)-4-methyl-2-cyclohexen-1-one was obtained in the form of a colorless oil. Yield: 75%

Aufarbeitung

  1. customThe resulting mixture was reacted at 50° C. for 24 hours
  2. extractionfollowed by extraction with dichloromethane
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by chromatography on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-7b185d254de647ad8e2b120ff2ebbe70
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06228893B1

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