3',5-Dimethoxy[1,1'-biphenyl]-2-carboxylic acid → 3,6-Dimethoxyfluoren-9-one

HRID 1871630Notes

Reaction equation

HRID 1871630 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][CH:13]=1)([OH:3])=O>CS(O)(=O)=O>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]2[C:1](=[O:3])[C:13]3[C:12]([C:5]=2[CH:6]=1)=[CH:17][C:16]([O:18][CH3:19])=[CH:15][CH:14]=3

Participants

3

Reactant 1

HCID 134616943',5-Dimethoxy[1,1'-biphenyl]-2-carboxylic acid

Product 1

HCID 2579393,6-Dimethoxyfluoren-9-oneYield 96%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

7.5 g of 2-carboxy-5,5'-dimethoxybiphenyl was dissolved in 75 mL of methanesulfonic acid to obtain a dark brown solution. The solution was stirred at room temperature for one hour, heated at 40°-50° C. for 5 hours and then cooled to room temperature. The reaction mixture was then poured onto crushed ice to form a yellow colored precipitate which was collected by filtration. The precipitate was washed with large amounts of water and then air dried to yield 6.7 g of crude 3,6-dimethoxy-9-fluorenone. Recrystallization from ethanol followed by column chromatography on silica gel using methylene chloride as the eluent yielded pure 3,6-dimethoxy-9-fluorenone. The structure was confirmed by NMR and mass spectroscopy.

Workup

  1. customto obtain a dark brown solution
  2. temperatureheated at 40°-50° C. for 5 hours
  3. temperaturecooled to room temperature
  4. additionThe reaction mixture was then poured
  5. customonto crushed ice
  6. customto form a yellow colored precipitate which
  7. filtrationwas collected by filtration
  8. washThe precipitate was washed with large amounts of water
  9. customair dried

Sources & evidence

ORD record
ord-c867e759f2334c11b9a4e37ca5a4714d
Source dataset
uspto-grants-2000_08
Patent number
US06103912

Reaction notes

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