Ethylene Glycol → 2-(4-Bromophenyl)-1,3-dioxolane

HRID 277347

Reaktionsgleichung

Reaktionsgleichung von HRID 277347
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:22](O)[CH2:23][OH:24].O>C1C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]2[O:24][CH2:23][CH2:22][O:7]2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 174Ethylene GlycolHCID 962WaterHCID 707414-BromobenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 27738422-(4-Bromophenyl)-1,3-dioxolane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-Bromobenzaldehyde (3 g, 0.0162 mol) in benzene (60 mL) was treated with p-toluenesulfonic acid monohydrate (0.15 g, 0.79 mmol) and ethylene glycol (5 mL, 0.0896 mol). The reaction was refluxed under nitrogen with azeotropic removal of water. After 3 hours, the reaction was cooled to room temperature and diluted with an equal volume of ethyl acetate. This solution was washed twice with aqueous bicarbonate, dried over magnesium sulfate and concentrated under reduced pressure. A colorless oil was recovered. Yield=2.83 g (92%). TLC (5% ethyl acetate in hexanes) showed clean product, Rf=0.17.

Aufarbeitung

  1. washThis solution was washed twice with aqueous bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customA colorless oil was recovered

Quellen und Nachweise

ORD-Eintrag
ord-84621f6afa09447c93b1caa0b9e5a63f
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355803B1

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