1-Propanol → 4-Ethenylphenyl-di-n-propoxymethane

HRID 327753

Reaktionsgleichung

Reaktionsgleichung von HRID 327753
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1)=[CH2:2].[CH2:11]([OH:14])[CH2:12][CH3:13].[C:15]1(C)[CH:20]=CC(S(O)(=O)=O)=C[CH:16]=1.[OH-].[Na+]>C1C=CC=CC=1.CCOCC.O>[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]([O:14][CH2:11][CH2:12][CH3:13])[O:8][CH2:16][CH2:15][CH3:20])=[CH:5][CH:4]=1)=[CH2:2]

Komponenten

8

Edukt 4

HCID 10311-PropanolHCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 393894-Vinylbenzaldehyde

Produkt 1

HCID 197335634-Ethenylphenyl-di-n-propoxymethane

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

In a 100 ml 3-necked round-bottomed flask, 6.8 g (51.5 mmol) of 4-vinylbenzaldehyde, 12.4 g (205.8 mmol) of n-propanol and 0.1 g (0.5 mmol) of p-toluenesulfonic acid are dissolved in 45 ml of benzene. The solution is refluxed for 22 hours using a water separator and then ether is added thereto. The mixture is subsequently neutralised with 0.1N sodium hydroxide solution. The organic phase is then washed three times with water, dried over magnesium sulfate and concentrated. The resulting oil can be purified by column chromatography (stationary phase silica gel, mobile phase hexane/ether 5/4) to yield 2.54 g (10.8 mmol, 21% of the theoretical yield) of the desired substance in the form of a clear oil.

Aufarbeitung

  1. temperatureThe solution is refluxed for 22 hours
  2. washThe organic phase is then washed three times with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resulting oil can be purified by column chromatography (stationary phase silica gel, mobile phase hexane/ether 5/4)
  6. customto yield 2.54 g (10.8 mmol, 21% of the
  7. customtheoretical yield) of the desired substance in the form of a clear oil

Quellen und Nachweise

ORD-Eintrag
ord-ae10a3d48b63427d8c466b82ddd5b310
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05274060

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