Carbon Dioxide → HCID 19978414, compound

HRID 1089849Notes

Reaction equation

HRID 1089849 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[C:16]2[CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1.C([Li])CCC.[C:22](=[O:24])=[O:23]>C1COCC1.O.C(OCC)(=O)C>[CH3:1][O:2][CH2:3][C:4]1[C:16]2[CH:15]([C:22]([OH:24])=[O:23])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 280Carbon DioxideHCID 601314HCID 601314, compoundHCID 178418339Butyllithium

Product 1

HCID 19978414HCID 19978414, compoundYield 33.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-methoxymethylfluorene (4.5 g, 21.4 mmol) in 100 mL of THF at -78° C. was charged with butyl lithium (10.0 mL, 23.5 mmol). The reaction mixture was stirred for 15 min, then CO2 gaseous (5g, 113.6 mmol) was introduced via cannula over a period 15 min at -78° C. The reaction mixture was warmed up to room temperature and stirred for additional 2 hr until colorless, 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 resulting precipitate was collected, washed with water and dried to give 1-methoxymethyl-9-fluorenecarboxylic acid (1.8 g, 33.1%).

Workup

  1. stirringstirred for additional 2 hr until colorless,
  2. customThe layers were separated
  3. washthe water layer was washed with ethyl acetate (3×50 mL)
  4. customThe resulting precipitate was collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-e3249d48b4d8476386f9227dea928753
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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