Diphenic acid → 9-Oxofluorene-4-carboxylic acid

HRID 745299

Reaction equation

HRID 745299 reaction equation
[C:1]1([C:10]2[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:12]([OH:14])=[O:13])[C:2](=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:3]([OH:5])=O>S(=O)(=O)(O)O>[CH:8]1[CH:9]=[C:1]2[C:10]3[C:11]([C:12]([OH:14])=[O:13])=[CH:15][CH:16]=[CH:17][C:18]=3[C:3](=[O:5])[C:2]2=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 10210Diphenic acid

Product 1

HCID 803619-Oxofluorene-4-carboxylic acidYield 100.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Diphenic acid (500 g, 2.06 Mol) was reacted with concentrated sulfuric acid (1250 mL, S.G. 1.84) at 140° C. for 35 minutes following the procedure of Huntress et al.1The red solution was cooled and precipitated by pouring the mixture into 15 L of distilled water. The yellow precipitate was boiled with 10 L of water, filtered and boiled with a further 10 L of water. The dried yellow product 9-fluorenone-4-carboxylic acid (463 g, 81% yield) was used in the next step without further purification.

Workup

  1. temperaturewas cooled
  2. customprecipitated
  3. additionby pouring the mixture into 15 L of distilled water
  4. filtrationfiltered

Sources & evidence

ORD record
ord-cb33cbd7758b40ac9dfad64fbe2cccfc
Source dataset
uspto-grants-1986_07
Patent number
US04598137

Linked notes

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