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

HRID 344282

Reaktionsgleichung

Reaktionsgleichung von HRID 344282
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([OH:15])[CH2:13][OH:14].[Br:16][CH2:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O>C1C=CC=CC=1>[CH2:13]1[CH2:12][O:15][C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([CH2:18][CH2:17][Br:16])[O:14]1

Komponenten

5

Edukt 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 1224323-Bromo-1-phenylpropan-1-one

Produkt 1

HCID 137641292-(2-Bromoethyl)-2-phenyl-1,3-dioxolaneAusbeute 49,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

p-Toluenesulfonic acid in a catalytic amount and ethylene glycol (2.9 g) were added to a solution of 3-bromo-1-phenyl-1-propanone (10 g) in benzene (100 ml), and the mixture was stirred at refluxing temperature for 70 hr. The reaction mixture was washed successively with 10% aqueous potassium carbonate solution and brine, and dried. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to give 6.0 g of 3,3-ethylenedioxy-3-phenylpropyl bromide.

Aufarbeitung

  1. temperatureat refluxing temperature for 70 hr
  2. washThe reaction mixture was washed successively with 10% aqueous potassium carbonate solution and brine
  3. customdried
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3d1639f71d7a442cb18d5a4ee01ed1b6
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05864039

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