Benzene → Trans-4-(acetylthio)-2-phenyl-1,3-dioxane

HRID 381417Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 381417
[C:1]1([C@H:7]2[O:12][C@@H:11](OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:10][CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:24]([O-:27])(=[S:26])[CH3:25].[Na+].C1C=CC=CC=1>CN(C)C=O>[C:24]([S:26][C@@H:11]1[CH2:10][CH2:9][O:8][C@@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:12]1)(=[O:27])[CH3:25]

Komponenten

5

Edukt 3

HCID 241BenzeneHCID 23700354HCID 23700354, VerbindungHCID 86583790cis-2-Phenyl-4-(p-toluenesulfonyloxy)-1,3-dioxane

Produkt 1

HCID 86583806Trans-4-(acetylthio)-2-phenyl-1,3-dioxaneAusbeute 43,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
117.5 °C

Versuchsvorschrift

In 200 ml of dimethylformamide were dissolved 29.0 g (86.8 mmol) of cis-2-phenyl-4-(p-toluenesulfonyloxy)-1,3-dioxane and 17.0 g (149 mmol) of sodium thioacetate, and the solution was heated at 115 to 120° C. under a nitrogen atmosphere for 1 hour. After cooling, benzene was added to the reaction mixture and the mixture was washed with water, followed by evaporation of the solvent. The thus obtained brown residue was subjected to column chromatography using silica gel and the fractions eluted with a mixed solvent of benzene-hexane (2:1) were collected, followed by recrystallization from a mixed solvent of benzene-hexane to obtain 8.99 g (yield: 43%) of the title compound having a melting point of 95 to 96° C.

Aufarbeitung

  1. temperatureAfter cooling
  2. washthe mixture was washed with water
  3. customfollowed by evaporation of the solvent
  4. washthe fractions eluted with a mixed solvent of benzene-hexane (2:1)
  5. customwere collected
  6. customfollowed by recrystallization from a mixed solvent of benzene-hexane

Quellen und Nachweise

ORD-Eintrag
ord-a4f5c64bc10e4ceabe13d7d6b868c92e
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06306880B1

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