Carbon Dioxide → 2,7-Dimethyl-9H-fluorene-9-carboxylic acid

HRID 1089841Notes

Reaction equation

HRID 1089841 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([CH3:15])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.C([Li])CCC.[C:21](=[O:23])=[O:22]>C1COCC1.O>[CH3:15][C:8]1[CH:9]=[CH:10][C:11]2[C:12]3[C:4](=[CH:3][C:2]([CH3:1])=[CH:14][CH:13]=3)[CH:5]([C:21]([OH:23])=[O:22])[C:6]=2[CH:7]=1

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 1013472,7-DimethylfluoreneHCID 178418339Butyllithium

Product 1

HCID 3483962,7-Dimethyl-9H-fluorene-9-carboxylic acidYield 72.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,7-dimethylfluorene (5.0 g, 25.7 mmol) in THF (100 mL) at -78° C. was charged with butyl lithium (16.8 mL, 26.0 mmol). The reaction mixture was stirred for 15 min, then CO2 gaseous (5g, 113.6 mmol) was introduced with cannula over a period of 15 min at -78° C. The reaction mixture Was Warmed up to room temperature and stirred overnight, diluted with water (150 mL). The layers were separated, the water layer was washed with ethyl acetate (5×20 mL), then acidified with conc. HCl. The precipitate formed was collected, washed with water and dried to give 4.4 g of 2,7-dimethyl-9-fluorenecarboxylic acid (72.4%).

Workup

  1. stirringstirred overnight
  2. customThe layers were separated
  3. washthe water layer was washed with ethyl acetate (5×20 mL)
  4. customThe precipitate formed
  5. customwas collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-a92e8b708e0a4d9197a5cd365e99bc21
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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