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

HRID 127932

Reaktionsgleichung

Reaktionsgleichung von HRID 127932
[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].C1(C)C=CC=CC=1.[CH2:20](O)[CH2:21][OH:22]>C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:7]1([C:5]2([CH2:4][CH2:3][CH2:2][Cl:1])[O:22][CH2:21][CH2:20][O:6]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 174Ethylene Glycol2×HCID 1140TolueneHCID 2535334-Chlorobutyrophenone

Produkt 1

HCID 128663382-(3-Chloropropyl)-2-phenyl-1,3-dioxolaneAusbeute 121,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6101p-Toluenesulfonic acidKatalysator

Versuchsvorschrift

A mixture of 36.5 g (0.2 mole) of γ-chlorobutyrophenone, 14 g of ethylene glycol (0.25 mole), 125 ml of toluene, and 0.1 g of p-toluenesulfonic acid is refluxed under a Dean-Stark trap for 1 hr. An additional 4 g of ethylene glycol is added and reflux continued for 3 hrs more. After cooling, the reaction mixture is washed with 5% sodium bicarbonate solution, dried with anhydrous magnesium sulfate, and concentrated. Upon standing at -10° C. overnight, the mixture partially crystallizes. The crystalline product is filtered and washed with petroleum ether to afford 17.7 g of 2-phenyl-2-(3'-chloropropyl)dioxolane, m.p. 56°-58°.

Aufarbeitung

  1. temperatureis refluxed under a Dean-Stark trap for 1 hr
  2. temperaturereflux
  3. temperatureAfter cooling
  4. washthe reaction mixture is washed with 5% sodium bicarbonate solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. waitUpon standing at -10° C. overnight
  8. customthe mixture partially crystallizes
  9. filtrationThe crystalline product is filtered
  10. washwashed with petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-6672789bd1dd4593997e3851704b24af
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04258045

Verknüpfte Notizen

Wird geladen…