Chrysene → 1-Chrysen-6-ylethanone

HRID 1193736

Reaktionsgleichung

Reaktionsgleichung von HRID 1193736
[CH:1]1[C:18]2[CH:17]=[CH:16][C:15]3[C:6](=[CH:7][CH:8]=[C:9]4[C:14]=3[CH:13]=[CH:12][CH:11]=[CH:10]4)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[CH3:23][C:24](Cl)=[O:25].C1([N+]([O-])=O)C=CC=CC=1>C(Cl)Cl>[C:24]([C:8]1[CH:7]=[C:6]2[C:15](=[C:14]3[C:9]=1[CH:10]=[CH:11][CH:12]=[CH:13]3)[CH:16]=[CH:17][C:18]1[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=1)(=[O:25])[CH3:23].[C:24]([C:12]1[CH:11]=[CH:10][C:9]2[CH:8]=[CH:7][C:6]3[C:15]([C:14]=2[CH:13]=1)=[CH:16][CH:17]=[C:18]1[C:5]=3[CH:4]=[CH:3][CH:2]=[CH:1]1)(=[O:25])[CH3:23]

Komponenten

5

Edukt 2

HCID 9171ChryseneHCID 131715424AlCl3 CH3COCl PhNO2

Produkt 2

HCID 1903171-Chrysen-6-ylethanoneHCID 124439383-Acetylchrysene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Friedel-Crafts reaction of chrysene with AlCl3 /CH3COCl/PhNO2 gave a mixture of 2-, 3-, and 6-acetylchrysenes (285 g, Cambridge Chemical, Inc.). This was stirred and heated in CH2Cl2 (400 mL) and then filtered. The insoluble material, 2-acetylchrysene, was washed copiously with CH2Cl2. The solvent was removed from the filtrate. The resulting solid was dissolved in PhCH3, then the mixture containing the remaining two isomers chromatographed using PhCH3 as eluting solvent on a plug of SiO2 (1 kg). The faster eluting isomer is 6-acetylchrysene while the slower is 3-acetylchrysene. The chromatography gave 132 g of impure 6-acetylchrysene, and 76 g of impure 3-acetylchrysene. These materials were used without further purification. Pure samples of the compounds were obtained by preparative HPLC using PhCH3 as the eluting solvent.

Aufarbeitung

  1. customgave
  2. filtrationfiltered
  3. washThe insoluble material, 2-acetylchrysene, was washed copiously with CH2Cl2
  4. customThe solvent was removed from the filtrate
  5. dissolutionThe resulting solid was dissolved in PhCH3
  6. additionthe mixture containing the remaining two isomers
  7. customchromatographed
  8. washas eluting solvent on a plug of SiO2 (1 kg)
  9. washThe faster eluting isomer

Quellen und Nachweise

ORD-Eintrag
ord-7c4126f6cef14df9a4386784a0f1d3fb
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04810727

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