HCID 178418268, compound → 9,10-Anthracenedicarboxaldehyde

HRID 128074

Reaction equation

HRID 128074 reaction equation
[CH:1]1[C:14]2[C@H:13]3[CH:15]([OH:18])[CH:16]([OH:17])[C@H:6]([C:7]4[C:12]3=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C(O)(=O)C>[CH:1]1[C:14]2[C:5](=[C:6]([CH:16]=[O:17])[C:7]3[C:12]([C:13]=2[CH:15]=[O:18])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 178418268HCID 178418268, compoundHCID 178516898HCID 178516898, compound

Product 1

HCID 815009,10-Anthracenedicarboxaldehyde

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2.38 g. (0.01 mole) of cis-9,10-dihydro-9,10-ethanoanthracene-11,12-diol [Newman et al., J. Am. Chem. Soc., 77, 3789 (1955)] in 50 ml. of glacial acetic acid was stirred magnetically at 30°-35° C. and treated portionwise with 8.9 g. (0.02 mole) of lead tetra-acetate or until a blue color persisted with starch-iodide test paper. The reaction mixture was stirred for two hours and the so-formed orange crystals were removed by filtration and recrystallized from methylene chloride giving 1.5 g. (65%) of orange needles, m.p. 245°-247° C.

Workup

  1. additiontreated portionwise with 8.9 g
  2. customthe so-formed orange crystals were removed by filtration
  3. customrecrystallized from methylene chloride giving 1.5 g

Sources & evidence

ORD record
ord-b7fb5b97a1bc47c2ab4c63c07d643463
Source dataset
uspto-grants-1981_03
Patent number
US04258181

Linked notes

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