2-(4-Chloro-2-methylphenyl)benzoic acid → 2-Chloro-4-methyl-fluoren-9-one

HRID 1799014Notes

Reaction equation

HRID 1799014 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([OH:16])=O)=[CH:10][CH:11]=[CH:12][CH:13]=2)=[C:4]([CH3:17])[CH:3]=1.CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:17])[C:5]2[C:8]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:14](=[O:16])[C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 532183582-(4-Chloro-2-methylphenyl)benzoic acidHCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 594925722-Chloro-4-methyl-fluoren-9-oneYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Under anhydrous calcium chloride drying conditions, a mixture of 4′-chloro-2′-methyl-biphenyl-2-carboxylic acid (21.60 g) and Eaton's reagent (7.7 w/w % solution of phosphorus pentoxide in methanesulfonic acid) (170 ml) was stirred at 100° C. for 2.5 hr. The reaction mixture was ice-cooled, water (500 ml) was slowly added dropwise, and the mixture was further stirred at room temperature for 10 min. This suspension was filtered, the obtained solid was mixed with 30 v/v % aqueous ethanol solution (200 ml), and the slurry was stirred at room temperature for 10 min, and filtered. The obtained solid was air-dried and dried under reduced pressure at 80° C. to give the title compound (19.744 g, 99%).

Workup

  1. temperaturecooled
  2. stirringthe mixture was further stirred at room temperature for 10 min
  3. filtrationThis suspension was filtered
  4. additionthe obtained solid was mixed with 30 v/v % aqueous ethanol solution (200 ml)
  5. stirringthe slurry was stirred at room temperature for 10 min
  6. filtrationfiltered
  7. customThe obtained solid was air-dried
  8. customdried under reduced pressure at 80° C.

Sources & evidence

ORD record
ord-0e823407839a43a0848e257a7987f3a1
Source dataset
uspto-grants-2013_01
Patent number
US08343994B2

Reaction notes

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