Ethylene Glycol → 2-(5-Chloro-2-nitrophenyl)-1,3-dioxolane

HRID 1487191

Reaktionsgleichung

Reaktionsgleichung von HRID 1487191
O.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7]([CH:10]=1)[CH:8]=[O:9].[CH2:14](O)[CH2:15][OH:16].ClCCl>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7]([CH:8]2[O:16][CH2:15][CH2:14][O:9]2)[CH:10]=1

Komponenten

7

Edukt 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6344DichloromethaneHCID 811235-Chloro-2-nitrobenzaldehyde

Produkt 1

HCID 2673852-(5-Chloro-2-nitrophenyl)-1,3-dioxolaneAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

In a flask equipped with a Dean-Stark water separator, 5-chloro-2-nitrobenzaldehyde (12.0 g, 64.7 mmol), ethylene glycol (8.0 g, 129.3 mmol) and p-toluenesulfonic acid (0.2 g) were dissolved in toluene (150 mL). The mixture was stirred at reflux for 8 hours. Dichloromethane was added and the organic phase was washed with saturated sodium bicarbonate and brine, then dried over anhydrous sodium sulfate, evaporated and purified by silica gel chromatography to afford the product 2-(5-chloro-2-nitrophenyl)-1,3-dioxolane (13.4 g, yield 90.0%).

Aufarbeitung

  1. temperatureat reflux for 8 hours
  2. washthe organic phase was washed with saturated sodium bicarbonate and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3628717df63f43608aef6ebf813b0d85
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09428508B2

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