Ethylene Glycol → 2-(3-Chloropropyl)-2-phenyl-1,3-dioxolane

HRID 848233

Reaktionsgleichung

Reaktionsgleichung von HRID 848233
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[CH2:13](O)[CH2:14][OH:15].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[Cl:1][CH2:2][CH2:3][CH2:4][C:5]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:15][CH2:14][CH2:13][O:6]1

Komponenten

6

Edukt 4

HCID 174Ethylene Glycol2×HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 2535334-Chlorobutyrophenone

Produkt 1

HCID 128663382-(3-Chloropropyl)-2-phenyl-1,3-dioxolane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of γ-chlorobutyrophenone (33.2 g; 0.182 mol), ethylene glycol (20.3 ml; 0.363 mol), p-toluenesulfonic acid (a pinch) and toluene (300 ml) is heated at reflux for 40 hours, and the water formed in the reaction is azeotroped off. After 20 hours, more ethylene glycol (20.3 ml; 0.363 mol) is added. On completion of the reaction the mixture is extracted with saturated aqueous sodium bicarbonate solution (300 ml), the organic layer is washed with 1 N sodium hydroxide solution and then with water, and is evaporated to afford 37.0 g of a cream colored solid, m.p. 54°-55.5° C.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 40 hours
  3. customis azeotroped off
  4. customOn completion of the reaction the mixture
  5. extractionis extracted with saturated aqueous sodium bicarbonate solution (300 ml)
  6. washthe organic layer is washed with 1 N sodium hydroxide solution
  7. customwith water, and is evaporated
  8. customto afford 37.0 g of a cream

Quellen und Nachweise

ORD-Eintrag
ord-be9f57e079234de7b59a4a89c743a87c
Quelldatensatz
uspto-grants-1981_10
Patentnummer
US04294986

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