HCID 178418268, compound → 9,10-Dihydro-9,10-anthracenedicarboxaldehyde

HRID 225207Notes

Reaction equation

HRID 225207 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[CH:13]([CH:15]=[O:18])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]([CH:16]=[O:17])[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 178418268HCID 178418268, compoundHCID 178516898HCID 178516898, compound

Product 1

HCID 112300969,10-Dihydro-9,10-anthracenedicarboxaldehyde

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
15 °C

Procedure

A mixture of 2.38 g. of cis-9,10-dihydro-9,10-ethanoanthracene-11,12-diol in 40 ml. of glacial acetic acid at room temperature is treated portionwise with 4.8 g. of lead tetraacetate, with stirring over a period of 10 minutes. The mixture is cooled to 15° C. and the solid which forms is collected by filtration, washed once with glacial acetic acid, then thoroughly with water giving the desired product as colorless grains, m.p. 144°-146° C.

Workup

  1. additionA mixture of 2.38 g
  2. filtrationthe solid which forms is collected by filtration
  3. washwashed once with glacial acetic acid

Sources & evidence

ORD record
ord-40cafc166c2f41e9bf5d18089138729b
Source dataset
uspto-grants-1980_11
Patent number
US04235996

Reaction notes

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