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2'-Methyl-biphenyl-2,4'-dicarboxylic acid → 4-methyl-9-oxo-9H-fluorene-2-carboxylic acid

HRID 1799022
Notes
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Reaction equation

HRID 1799022 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]1[C:12]([C:17](O)=[O:18])=[CH:13][CH:14]=[CH:15][CH:16]=1>O>[CH3:1][C:2]1[C:3]2[C:11]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:17](=[O:18])[C:4]=2[CH:5]=[C:6]([C:8]([OH:10])=[O:9])[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 594924972'-Methyl-biphenyl-2,4'-dicarboxylic acid

Product 1

HCID 594925644-methyl-9-oxo-9H-fluorene-2-carboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2′-methyl-biphenyl-2,4′-dicarboxylic acid (1.94 g) and polyphosphoric acid (50 g) was stirred at 180° C. for 3 hr. The reaction mixture was cooled to room temperature, water (100 ml) was slowly added dropwise, and the mixture was further stirred at room temperature for 10 min. This suspension was filtered, and the obtained solid was successively washed with water (50 ml) and 50 v/v % aqueous methanol solution (50 ml). The obtained solid was air-dried, and dried under reduced pressure at 80° C. to give the title compound (1.745 g, 97%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringthe mixture was further stirred at room temperature for 10 min
  3. filtrationThis suspension was filtered
  4. washthe obtained solid was successively washed with water (50 ml) and 50 v/v % aqueous methanol solution (50 ml)
  5. customThe obtained solid was air-dried
  6. customdried under reduced pressure at 80° C.

Sources & evidence

ORD record
ord-bde43fa7d41d4710b1696f6d41905484
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08343994B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes