Nitrobenzene → Dimethyl phenanthrene-3,4-dicarboxylate

HRID 379539

Reaction equation

HRID 379539 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1)=[CH2:2].[C:13]([C:18]([O:20][CH3:21])=[O:19])#[C:14][C:15]([O-:17])=[O:16].[N+]([C:25]1C=CC=CC=1)([O-])=O>>[CH:1]1[C:3]2[CH:12]=[CH:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]=2[C:13]([C:18]([O:20][CH3:21])=[O:19])=[C:14]([C:15]([O:17][CH3:25])=[O:16])[CH:2]=1

Participants

4

Reactant 3

HCID 7416NitrobenzeneHCID 132302-VinylnaphthaleneHCID 86613298HCID 86613298, compound

Product 1

HCID 15075419Dimethyl phenanthrene-3,4-dicarboxylate

Procedure

A solution of 65 mmol of 2-vinylnaphthalene and 68 mmol of methyl acetylene-dicarboxylate in 200 ml of nitrobenzene is maintained at reflux for 14 hours. After distillation of the solvent, the reaction medium is chromatographed on silica (eluent: CH2Cl2) in order to obtain the expected product.

Workup

  1. temperatureat reflux for 14 hours
  2. distillationAfter distillation of the solvent
  3. customthe reaction medium is chromatographed on silica (eluent: CH2Cl2) in order

Sources & evidence

ORD record
ord-f13ee31e844043908b56df1cb1976e0b
Source dataset
uspto-grants-2001_10
Patent number
US06300340B1

Linked notes

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