cis-2-Chloro-9,10-dihydro-9,10-ethanoanthracene-11,12-diol → 2-Chloro-9,10-dihydro-9,10-anthracenedicarboxaldehyde

HRID 225210Notes

Reaction equation

HRID 225210 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[C@@H:12]3[CH:16]([OH:19])[CH:17]([OH:18])[C@@H:5]([C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:4]=2[CH:3]=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C(O)(=O)C>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[CH:12]([CH:16]=[O:19])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]([CH:17]=[O:18])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 53990653cis-2-Chloro-9,10-dihydro-9,10-ethanoanthracene-11,12-diolHCID 178418268HCID 178418268, compound

Product 1

HCID 233296042-Chloro-9,10-dihydro-9,10-anthracenedicarboxaldehyde

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2.7 g. of cis-2-chloro-9,10-dihydro-9,10-ethanoanthracene-11,12-diol in 20 ml. of acetic acid at room temperature is added 5.0 g. of lead tetraacetate (containing 10% acetic acid) portionwise. The mixture is stirred for 10 minutes, cooled in an ice-water bath and the crystals which form are collected by filtration and washed with cold acetic acid, giving the desired product as off-white crystals, m.p. 113°-115° C.

Workup

  1. temperaturecooled in an ice-water bath
  2. filtrationthe crystals which form are collected by filtration
  3. washwashed with cold acetic acid

Sources & evidence

ORD record
ord-f7c576f1432646d5b99495aeeae3f802
Source dataset
uspto-grants-1980_11
Patent number
US04235996

Reaction notes

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