Ethyl Acetate → 2-Methoxy-9-fluorenecarboxylic acid

HRID 1089831Notes

Reaction equation

HRID 1089831 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][C:5]=2[CH:4]=1.C([Li])CCC.[C:21]([O:24]CC)(=[O:23])C>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]([C:21]([OH:24])=[O:23])[C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 173012-MethoxyfluoreneHCID 178418339Butyllithium

Product 1

HCID 199784192-Methoxy-9-fluorenecarboxylic acidYield 66.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-methoxyfluorene (2.7 g, 13.8 mmol) in 50 mL of THF at -78° C. was charged with n-butyl lithium (0.93 g, 14.5 mmol). The reaction mixture was stirred for 15 min then CO, gaseous (5 g, 113.6 mmol) was introduced via 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 a colorless solution was obtained. The reaction mixture was diluted with 100 mL of water and 100 mL of ethyl acetate. The layers were separated, the aqueous phase was washed with ethyl acetate (5×25 mL) and acidified to pH 1 with concentrated hydrochloric acid. The precipitate was filtered off, washed with water and dried to afford 2.2 g (66.7%) of 2-methoxy-9-fluorenecarboxylic acid as colorless solid.

Workup

  1. additionCO, gaseous (5 g, 113.6 mmol) was introduced via cannula over a period of 15 min at -78° C
  2. stirringstirred for additional 2 hr until a colorless solution
  3. customwas obtained
  4. customThe layers were separated
  5. washthe aqueous phase was washed with ethyl acetate (5×25 mL)
  6. filtrationThe precipitate was filtered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-587f96487ccd4b4c90eaec63b207938c
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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