Carbon Dioxide → 2-Methyl-9-fluorenecarboxylic acid

HRID 1089827Notes

Reaction equation

HRID 1089827 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.C([Li])CCC.[C:20](=[O:22])=[O:21]>C1COCC1.O.C(OCC)(=O)C>[CH3:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]([C:20]([OH:22])=[O:21])[C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 280Carbon DioxideHCID 150262-MethylfluoreneHCID 178418339Butyllithium

Product 1

HCID 199784182-Methyl-9-fluorenecarboxylic acidYield 81.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-methylfluorene (6 g, 33.2 mmol) in 100 ml of THF at -78° C. was charged with butyl lithium (2.18 g, 34.0 mmol). The reaction mixture was stirred for 15 min then CO2 gaseous (5 g, 113.6 mmol) was introduced via a cannula over a period of 15 min at -78° C. The reaction mixture was warmed up to room temperature and stirred for additional 2 hr until colorless. The reaction mixture was diluted with 250 mL of water and 100 mL of ethyl acetate, the layers were separated, the aqueous phase was washed with ethyl acetate (3×50 mL) and acidified to pH 2 with conc. HCl. The precipitate was filtered off, washed with water and dried to afford 6.1 g (81.9%) of 2-methyl-9-fluorenecarboxylic acid.

Workup

  1. stirringstirred for additional 2 hr until colorless
  2. customthe layers were separated
  3. washthe aqueous phase was washed with ethyl acetate (3×50 mL)
  4. filtrationThe precipitate was filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-593482eb2ea046c19959d94e40e1c5fe
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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