Carbon Dioxide → 1-Methyl-9-fluorenecarboxylic acid

HRID 1089837Notes

Reaction equation

HRID 1089837 reaction equation
[CH3:1][C:2]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:20](=[O:22])=[O:21]>C1COCC1.O.C(OCC)(=O)C>[CH3:1][C:2]1[C:14]2[CH:13]([C:20]([OH:22])=[O:21])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 280Carbon DioxideHCID 156041-MethylfluoreneHCID 178418339Butyllithium

Product 1

HCID 199784101-Methyl-9-fluorenecarboxylic acidYield 85%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-methylfluorene (3.8 g, 21.1 mmol) in 100 mL of THF at -78° C. was charged with n-butyl lithium (3.5M solution in hexane, 6.29 ml, 22.0 mmol). The reaction mixture was stirred for 15 min, then CO2 gaseous (5 g, 113.6 mmol) was introduced via cannula over a period of 15 min. The reaction mixture was warmed up to room temperature and stirring was continued until no color was apparent (approximately 2 hr). The slurry was diluted with water (100 mL) and ethyl acetate (50 mL). The layers were separated, the water layer was washed with ethyl acetate (3×50 mL), then acidified with conc. HCl. The precipitate was collected, washed with water and dried to give 1-methyl-9-fluorenecarboxylic acid (4.02 g, 84.8%).

Workup

  1. stirringstirring
  2. custom(approximately 2 hr)
  3. customThe layers were separated
  4. washthe water layer was washed with ethyl acetate (3×50 mL)
  5. customThe precipitate was collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-f21d9bdc285e4258903685dd07574cf8
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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