Ethylene Glycol → 2-[2-(Methoxycarbonyl)ethyl]-2-phenyl-1,3-dioxolane

HRID 1607400

Reaktionsgleichung

Reaktionsgleichung von HRID 1607400
[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:15](O)[CH2:16][OH:17].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1([O:17][CH2:16][CH2:15][O:13]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

5

Edukt 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 141190Benzenebutanoic acid, gamma-oxo-, methyl ester

Produkt 1

HCID 100371022-[2-(Methoxycarbonyl)ethyl]-2-phenyl-1,3-dioxolane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a solution of 2.0 g of 3-benzoylpropionic acid methyl ester in 50 ml of dry benzene were added 0.7 ml of ethylene glycol and 0.01 g of anhydrous-p-toluene-sulfonic acid and the mixture was heated under reflux for 17 hours while removing water formed during the reaction by using a molecular sieve. After cooling, the reaction mixture was washed with a saturated sodium chloride aqueous solution, and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: benzene/hexane=1/1 by volume) to obtain 1.8 g of 4,4-ethylenedioxy-4-phenylbutyric acid methyl ester.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 17 hours
  3. customwhile removing water
  4. customformed during the reaction
  5. temperatureAfter cooling
  6. washthe reaction mixture was washed with a saturated sodium chloride aqueous solution
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel flash column chromatography (eluent: benzene/hexane=1/1 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-17cb79a884504a5682a49f850efe5a25
Quelldatensatz
uspto-grants-1989_09
Patentnummer
US04863904

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