Anthracene-1,9-dicarboxylic acid → HCID 13155836, compound

HRID 1682501Notes

Reaction equation

HRID 1682501 reaction equation
[C:1]1([C:18]([OH:20])=[O:19])[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[C:15]([OH:17])=O)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1>C(OC(=O)C)(=O)C>[C:1]12[C:18](=[O:19])[O:20][C:15](=[O:17])[C:13]3=[C:14]1[C:5](=[CH:6][C:7]1[C:12]3=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH:4]=[CH:3][CH:2]=2

Participants

3

Reactant 1

HCID 13155838Anthracene-1,9-dicarboxylic acid

Product 1

HCID 13155836HCID 13155836, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A suspension of 6.5 g of anthracene-1,9-dicarboxylic acid (E. D. Bergmann and R. Ikan, J. Org. Chem., 23, 907 (1958)) in 100 ml of acetic anhydride was heated at reflux for 3 hours. The mixture was cooled and the orange precipitate was collected by filtration, washed with ether and dried in air to give 5.1 g (68%) of the title compound. Recrystallization from dimethylsulfoxide or toluene gave orange plates with melting point 289°-290° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperatureThe mixture was cooled
  4. filtrationthe orange precipitate was collected by filtration
  5. washwashed with ether
  6. customdried in air

Sources & evidence

ORD record
ord-b202df1b182f4ac9b03b1fde24d6f4c6
Source dataset
uspto-grants-1997_06
Patent number
US05635506

Reaction notes

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