Water → 3-(4-Isopropylphenyl)-2,2,4,6,7-pentamethyl-5-[4-(methylsulfinyl)benzyloxy]-2,3-dihydrobenzofuran

HRID 1743214Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1743214
I([O-])(=O)(=O)=O.[Na+].[CH:7]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[C:20]3[C:21]([CH3:37])=[C:22]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][C:32]([S:35][CH3:36])=[CH:31][CH:30]=4)[C:23]([CH3:26])=[C:24]([CH3:25])[C:19]=3[O:18][C:17]2([CH3:39])[CH3:38])=[CH:12][CH:11]=1)([CH3:9])[CH3:8].O.C(OCC)(=[O:43])C>C(O)C>[CH:7]([C:10]1[CH:11]=[CH:12][C:13]([CH:16]2[C:20]3[C:21]([CH3:37])=[C:22]([O:27][CH2:28][C:29]4[CH:30]=[CH:31][C:32]([S:35]([CH3:36])=[O:43])=[CH:33][CH:34]=4)[C:23]([CH3:26])=[C:24]([CH3:25])[C:19]=3[O:18][C:17]2([CH3:39])[CH3:38])=[CH:14][CH:15]=1)([CH3:9])[CH3:8]

Komponenten

6

Edukt 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 101617033-(4-Isopropylphenyl)-2,2,4,6,7-pentamethyl-5-(4-methylthiobenzyloxy)-2,3-dihydrobenzofuranHCID 23667635Sodium periodate

Produkt 1

HCID 102274693-(4-Isopropylphenyl)-2,2,4,6,7-pentamethyl-5-[4-(methylsulfinyl)benzyloxy]-2,3-dihydrobenzofuranAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Sodium periodate (0.766 g, 3.58 mmol) was added to a solution of 3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-5-(4-methylthiobenzyloxy)-2,3-dihydrobenzofuran (1.50 g, 3.26 mmol) in a mixture of ethanol (80 mL) and water (8 mol), and the mixture was heated under reflux for 2 hours. To the reaction mixture were added ethyl acetate and water to separate it into two layers, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was recrystallized from ethyl acetate-hexane to obtain the title compound (1.23 g, yield 79%).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customto separate it into two layers
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-e088e1d056954f488793c7417baec2e0
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07008950B1

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