Toluene → Chrysene-2-carbaldehyde

HRID 1762016

Reaction equation

HRID 1762016 reaction equation
[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]

Participants

4

Reactant 2

HCID 1140TolueneHCID 155993232-Hydroxymethylchrysene

Product 1

HCID 15599322Chrysene-2-carbaldehydeYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-a7b5b9d83e024489898298c178cee9c8
Source dataset
uspto-grants-1989_05
Patent number
US04829090

Linked notes

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