Benzene → 2-(Bromomethyl)-2,4-bis(4-chlorophenyl)-1,3-dioxolane

HRID 1390588Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1390588
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)=[O:4].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([OH:22])[CH2:20]O)=[CH:15][CH:14]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[Br:1][CH2:2][C:3]1([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=2)[O:22][CH:19]([C:16]2[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=2)[CH2:20][O:4]1

Komponenten

6

Edukt 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 68303p-Chlorophenacyl bromideHCID 1011071-(4-Chlorophenyl)-1,2-ethanediol

Produkt 1

HCID 203326202-(Bromomethyl)-2,4-bis(4-chlorophenyl)-1,3-dioxolane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

a mixture of 11.7 parts of 2-bromo-4'-chloroacetophenone, 9 parts of 1-(p-chlorophenyl)-1,2-ethanediol, 0.5 parts of p-toluenesulfonic acid and 80 parts of benzene is stirred and refluxed for 2 days with water-separator. The reaction mixture is cooled and washed successively twice with a sodium hydrogen carbonate solution and once with water. The organic phase is dried and evaporated. The residue is triturated in petroleum ether and cooled on ice. The precipitated product is filtered off, crystallized from methanol, stirred in acetonitrile while cooling on ice, filtered off again and washed once more with acetonitrile, yielding 2-(bromomethyl)-2,4-bis(p-chlorophenyl)-1,3-dioxolane.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled
  2. washwashed successively twice with a sodium hydrogen carbonate solution and once with water
  3. customThe organic phase is dried
  4. customevaporated
  5. customThe residue is triturated in petroleum ether
  6. temperaturecooled on ice
  7. filtrationThe precipitated product is filtered off
  8. customcrystallized from methanol
  9. stirringstirred in acetonitrile
  10. temperaturewhile cooling on ice
  11. filtrationfiltered off again
  12. washwashed once more with acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-c4db3aea653b469e866ac49da0c0f32f
Quelldatensatz
uspto-grants-1979_02
Patentnummer
US04139540

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