Water → 2-(4-Chlorophenyl)-2-(4-nitrophenyl)-1,3-dioxolane

HRID 564827

Reaktionsgleichung

Reaktionsgleichung von HRID 564827
[C:1]1([CH3:7])C=CC=CC=1.O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[O:17])=[CH:12][CH:11]=1.C1(C)C=CC(S(O)(=O)=[O:34])=CC=1>C(O)CO>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2([C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)[O:34][CH2:1][CH2:7][O:17]2)=[CH:14][CH:15]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 3477714-Chloro-4'-nitrobenzophenone

Produkt 1

HCID 154896262-(4-Chlorophenyl)-2-(4-nitrophenyl)-1,3-dioxolaneAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 174Ethylene GlycolLösungsmittel

Versuchsvorschrift

Toluene (1900 ml) was stirred in a round-bottom flask (51) using a water separator. (4-Chlorophenyl)(4-nitrophenyl)methanone (250 g) was added portionwise. p-Toluene-sulfonic acid (54.5 g) was added portionwise. Ethylene glycol (237.5 g) was poured out into the mixture. The mixture was stirred and refluxed for 48 hours. The solvent was evaporated. The residue was dissolved into ethyl acetate (5 l) and washed twice with a K2CO3 10% solution. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue was stirred in DIPE, filtered off and dried (vacuum, 40° C., 24 hours), yielding 265 g (91%) of 2-(4-chlorophenyl)-2-(4-nitrophenyl)-1,3-dioxolane (interm. 5-a).

Aufarbeitung

  1. temperaturerefluxed for 48 hours
  2. customThe solvent was evaporated
  3. dissolutionThe residue was dissolved into ethyl acetate (5 l)
  4. washwashed twice with a K2CO3 10% solution
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. stirringThe residue was stirred in DIPE
  10. filtrationfiltered off
  11. customdried (vacuum, 40° C., 24 hours)

Quellen und Nachweise

ORD-Eintrag
ord-f1a653b03e0c40d1ae8146d7d9fbdcab
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06169096A

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