2-Methoxypropene → (2,2-Dimethyl-1,3-dioxan-5-yl)methanol

HRID 228929

Reaktionsgleichung

Reaktionsgleichung von HRID 228929
[CH3:1][O:2][C:3]([CH3:5])=[CH2:4].[OH:6][CH2:7][CH:8](CO)[CH2:9][OH:10]>CN(C)C=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:4][C:3]1([CH3:5])[O:6][CH2:7][CH:8]([CH2:9][OH:10])[CH2:1][O:2]1

Komponenten

5

Edukt 2

HCID 83002-MethoxypropeneHCID 78432Trimethylolmethane

Produkt 1

HCID 3584869(2,2-Dimethyl-1,3-dioxan-5-yl)methanolAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-methoxypropene (1 g) in N,N-dimethylformamide (150 ml) was added to 2-(hydroxymethyl)-1,3-propanediol (500 mg). p-Toluenesulfonic acid (10 mg) was added thereto, and the mixture was stirred at room temperature overnight. The solvent was removed by distillation under the reduced pressure, water was added to the residue, and the mixture was extracted with n-butanol. The n-butanol layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using hexane-acetone to give (2,2-dimethyl[1,3]dioxan-5-yl)-methanol (378 mg, yield 55%).

Aufarbeitung

  1. customThe solvent was removed by distillation under the reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with n-butanol
  4. washThe n-butanol layer was then washed with water
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-286338b454554e4489efeb880c1dd36b
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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