2,2-Difluoropropane-1,3-diol → 1,3-Dioxane, 5,5-difluoro-2-[(phenylmethoxy)methyl]-

HRID 31670

Reaktionsgleichung

Reaktionsgleichung von HRID 31670
[F:1][C:2]([F:7])([CH2:5][OH:6])[CH2:3][OH:4].[CH2:8]([O:15][CH2:16][CH:17]=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:8]([O:15][CH2:16][CH:17]1[O:6][CH2:5][C:2]([F:7])([F:1])[CH2:3][O:4]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 957442,2-Difluoropropane-1,3-diolHCID 108989(Phenylmethoxy)acetaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 597924871,3-Dioxane, 5,5-difluoro-2-[(phenylmethoxy)methyl]-Ausbeute 42,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 2,2-difluoropropane-1,3-diol (1 g, 8.9 mmol), benzyloxyacetaldehyde (1.34 g, 8.9 mmol), p-toluenesulfonic acid monohydrate (154 mg, 0.81 mmol) and toluene (20 ml) was heated under reflux by a condenser equipped with a Dean-Stark apparatus for one hour. The resultant mixture was stirred at room temperature overnight and then the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and silica gel was added thereto. The resultant mixture was concentrated to dryness and subjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=10/1) to obtain the title compound (930 mg, 42.8%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux by a condenser
  3. customequipped with a Dean-Stark apparatus for one hour
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. additionsilica gel was added
  7. concentrationThe resultant mixture was concentrated to dryness
  8. washsubjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-97711e84e9294c079076706531e3404f
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425634B2

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