Toluene → Chrysene-2-carbaldehyde

HRID 2413572

Reaktionsgleichung

Reaktionsgleichung von HRID 2413572
[OH:1][CH2:2][C:3]1[CH:20]=[CH:19][C:18]2[C:17]3[C:8](=[C:9]4[C:14](=[CH:15][CH:16]=3)[CH:13]=[CH:12][CH:11]=[CH:10]4)[CH:7]=[CH:6][C:5]=2[CH:4]=1.C1(C)C=CC=CC=1>C(Cl)Cl>[CH:4]1[C:5]2[CH:6]=[CH:7][C:8]3[C:17](=[CH:16][CH:15]=[C:14]4[C:9]=3[CH:10]=[CH:11][CH:12]=[CH:13]4)[C:18]=2[CH:19]=[CH:20][C:3]=1[CH:2]=[O:1]

Komponenten

4

Edukt 2

HCID 1140TolueneHCID 155993232-Hydroxymethylchrysene

Produkt 1

HCID 15599322Chrysene-2-carbaldehydeAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Hydroxymethylchrysene (20C, 8.0 g, 0.031 mol) in CH2Cl2 (2.5 L) was treated with BaMnO4 (Aldrich, 15.9 g, 0.062 mol) and refluxed for 12 h. The reaction mixture was filtered, and concentrated to give a solid, which was then passed through a plug of SiO2 (500 g) using PhCH3 as the eluting solvent. The appropriate fractions were combined and the volume reduced to 75 mL to afford 6.98 g (88%) of chrysene-2-carbaldehyde mp 215°-216.5°, (C, H).

Aufarbeitung

  1. temperaturerefluxed for 12 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. customto give a solid, which

Quellen und Nachweise

ORD-Eintrag
ord-603366f9deed4dda98e4e3d53d30d030
Quelldatensatz
uspto-grants-1988_01
Patentnummer
US04719046

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