Toluene → Chrysene-2-carbaldehyde

HRID 1762016

Reaktionsgleichung

Reaktionsgleichung von HRID 1762016
[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-a7b5b9d83e024489898298c178cee9c8
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04829090

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