Methanol → 1,3-Dihydroxypropan-2-yl 4-methylbenzenesulfonate

HRID 381448Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 381448
C1([C@H]2O[C@@H:11]([O:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH2:10]CO2)C=CC=CC=1.[C:24]([O-])(O)=[O:25].[Na+].C[OH:30]>>[C:20]1([CH3:23])[CH:19]=[CH:18][C:17]([S:14]([O:13][CH:11]([CH2:10][OH:30])[CH2:24][OH:25])(=[O:15])=[O:16])=[CH:22][CH:21]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 86583790cis-2-Phenyl-4-(p-toluenesulfonyloxy)-1,3-dioxane

Produkt 1

HCID 103772501,3-Dihydroxypropan-2-yl 4-methylbenzenesulfonateAusbeute 100 %

Versuchsvorschrift

In 50 ml of methanol were dissolved 5.00 g of cis-2-phenyl-4-(p-toluenesulfonyloxy)-1,3-dioxane, and 5 ml of a 4N HC1-dioxane solution were added to the solution, followed by stirring of the resulting mixture at room temperature for 2 hours. To the reaction mixture were added 3.5 g of NaHCO3 powder, and the mixture was stirred for 10 minutes. Then, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The thus obtained oil was subjected to column chromatography using silica gel and eluted with ethyl acetate to obtain 3.70 g (yield: 100%) of the title compound as an oil.

Aufarbeitung

  1. additionwere added to the solution
  2. stirringthe mixture was stirred for 10 minutes
  3. filtrationThen, the reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. washeluted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c16dc367b8824636b51435fd08312b9c
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06306880B1

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