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Water → l-Acetoxy-5-hydroxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-9-(4-methylphenylsulfonyl)-nona-2,6-diene

HRID 1700049
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1700049
[OH:1][CH2:2][CH:3]=[C:4]([CH3:32])[CH2:5][CH:6]([OH:31])[CH:7]=[C:8]([CH3:30])[CH2:9][CH:10]([C:21]1[C:26]([CH3:28])([CH3:27])[CH2:25][CH2:24][CH2:23][C:22]=1[CH3:29])[S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12].C(=O)([O-])[O-].[Na+].[Na+].[C:39](OC(=O)C)(=[O:41])[CH3:40].O>CCCCCC.[Cl-].C([N+](C)(C)C)CCCCCCCCCCC>[C:39]([O:1][CH2:2][CH:3]=[C:4]([CH3:32])[CH2:5][CH:6]([OH:31])[CH:7]=[C:8]([CH3:30])[CH2:9][CH:10]([C:21]1[C:26]([CH3:27])([CH3:28])[CH2:25][CH2:24][CH2:23][C:22]=1[CH3:29])[S:11]([C:14]1[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=1)(=[O:12])=[O:13])(=[O:41])[CH3:40]
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Komponenten

7

Edukt 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 701693381,5-Dihydroxy-3,7-dimethyl-9-(2,6,6-trimehylcyclohexene-1-yl)-9-(4-methylphenysulfonyl)-nona-2,6-diene

Produkt 1

HCID 54036189l-Acetoxy-5-hydroxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-9-(4-methylphenylsulfonyl)-nona-2,6-diene
Ausbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8152Dodecyltrimethylammonium chlorideKatalysatorHCID 8058HexaneLösungsmittel

Versuchsvorschrift

In a dry flask, 60 mg (0.13 mmol) of 1,5-dihydroxy-3,7-dimethyl-9-(2,6,6-trimehylcyclohexene-1-yl)-9-(4-methylphenysulfonyl)-nona-2,6-diene (hereinafter, referred to as compound [IV-1]) was charged and dissolved in 20 ml of n-hexane, and 3.4 mg (0.013 mmol) of n-dodecyltrimethylammonium chloride, 14 mg (0.13 mmol) of sodium carbonate and 13.3 mg (0.13 mmol) of acetic anhydride were added thereto. After stirring at room temperature for twenty hours, disappearance of the starting material was confirmed, and then water was added to the reaction mass. After extracting with ether, the organic layer was washed with an aqueous solution of ammonium chloride and a saturated aqueous solution of sodium chloride in order. After drying over anhydrous magnesium sulfate, the organic layer was concentrated to give a crude product. The crude product was purified by silica gel chromatography to give l-acetoxy-5-hydroxy-3,7-dimethyl-9-(2,6,6-trimethylcyclohexene-1-yl)-9-(4-methylphenylsulfonyl)-nona-2,6-diene (hereinafter, referred to as compound [III-1]) in a yield of 92%.

Aufarbeitung

  1. addition) was charged
  2. extractionAfter extracting with ether
  3. washthe organic layer was washed with an aqueous solution of ammonium chloride
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. concentrationthe organic layer was concentrated
  6. customto give a crude product
  7. customThe crude product was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-951925395a8c4140a25662efa1524dd5
Quelldatensatz
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06348622B1

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