p-Toluenesulfonic acid → 2-(Bromomethyl)-4-[(4-chlorophenoxy)methyl]-2-(4-chlorophenyl)-1,3-dioxolane

HRID 1578433Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1578433
[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:24]=[CH:23][C:16]([O:17][CH2:18][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>[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]([CH2:18][O:17][C:16]2[CH:15]=[CH:14][C:13]([Cl:12])=[CH:24][CH:23]=2)[CH2:20][O:4]1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 7697ChlorphenesinHCID 68303p-Chlorophenacyl bromide

Produkt 1

HCID 203326492-(Bromomethyl)-4-[(4-chlorophenoxy)methyl]-2-(4-chlorophenyl)-1,3-dioxolane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of 11.7 parts of 2-bromo-4'-chloroacetophenone, 12.2 parts of 1-(p-chlorophenoxy)-2,3-propanediol, 3 parts of p-toluenesulfonic acid and 240 parts of benzene is stirred and refluxed for 20 hours in a four-necked round-bottom flask equipped with a watertrap. The benzene solution is washed successively with a diluted sodium hydroxide solution and with water. The solvent is removed in vacuo. The residue is triturated in methanol. The precipitated product is filtered off (methanol filtrate is set aside) and crystallized from toluene, yielding A-2-(bromomethyl-4-(p-chlorophenoxymethyl)-2-(p-chlorophenyl)-1,3-dioxolane; m.p. 165°C.

Aufarbeitung

  1. temperaturerefluxed for 20 hours in a four-necked round-bottom flask
  2. customequipped with a watertrap
  3. washThe benzene solution is washed successively with a diluted sodium hydroxide solution and with water
  4. customThe solvent is removed in vacuo
  5. customThe residue is triturated in methanol
  6. filtrationThe precipitated product is filtered off (methanol filtrate
  7. customcrystallized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-ed4f67585ce84caeb44a058025c132e3
Quelldatensatz
uspto-grants-1976_02
Patentnummer
US03936470

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