Ethylene Glycol → 2-(4-Ethenylphenyl)-1,3-dioxolane

HRID 327750

Reaktionsgleichung

Reaktionsgleichung von HRID 327750
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1)=[CH2:2].[CH2:11](O)[CH2:12][OH:13].C1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]2[O:13][CH2:12][CH2:11][O:8]2)=[CH:5][CH:4]=1)=[CH2:2]

Komponenten

6

Edukt 3

HCID 174Ethylene GlycolHCID 1140TolueneHCID 393894-Vinylbenzaldehyde

Produkt 1

HCID 132377022-(4-Ethenylphenyl)-1,3-dioxolaneAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

In a 250 ml 3-necked round-bottomed flask, 13.72 g of (103 mmol) of 4-vinylbenzaldehyde, 7.08 g (114 mmol) of ethylene glycol and 0.23 g (1.3 mmol) of p-toluenesulfonic acid are added to 100 ml of toluene. The resulting mixture is refluxed at 45° C. under reduced pressure for 3 hours using a water separator. It is then washed twice with 100 ml of water, and the organic phase is dried over magnesium sulfate and concentrated to yield 17.47 g of crude product in the form of a pale yellow oil. The latter is distilled at 80° C./0.05 mbar. Yield: 12.81 g (72.7 mmol, 70.6% of the theoretical yield). 1H-NMR (CDCl3, 100 mHz): δ7.39/s/4H, 6.68/dd (J1 =11 Hz, J2 =18 Hz)/1H, 5.74/s/1H, 5.72 (J1 =18 Hz, J2 =2 Hz)/1H, 5.22/dd (J1 =11 Hz, J2 =2 Hz)/1H, 3.96/m/4H.

Aufarbeitung

  1. washIt is then washed twice with 100 ml of water
  2. dry with materialthe organic phase is dried over magnesium sulfate
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f33dcf1aaee94fef935f9252201ee96f
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05274060

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