Ethyl Acetate → 2-methoxyfluoren-9-one

HRID 1089829Notes

Reaction equation

HRID 1089829 reaction equation
O[C:2]1[C:3](=O)[C:4]2[C:12](=[CH:13][CH:14]=1)[C:11]1[C:6](=[CH:7]C=C[CH:10]=1)[CH:5]=2.[OH-:16].[Na+].[C:18]([O:21][CH2:22][CH3:23])(=O)C>C(Cl)Cl.O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC>[CH3:18][O:21][C:22]1[CH:23]=[CH:10][C:11]2[C:12]3[C:4](=[CH:3][CH:2]=[CH:14][CH:13]=3)[C:5](=[O:16])[C:6]=2[CH:7]=1

Participants

8

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 136385905HCID 136385905, compound

Product 1

HCID 2454892-methoxyfluoren-9-oneYield 71%

Reagents, catalysts & solvents 4

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

A solution of 2-hydroxyfluorenone (5 g, 25 5 mmol) in 500 mL methylene chloride was charged with 100 mL solution of 1N NaOH (4 g, 100 mmol), a solution of p-methyl tosylate (9.5 g, 51 mmol) in 200 mL of water and tetrabutylammonium hydrogen sulfate (0.2 g, catalytic) at room temperature. The reaction was monitored by TLC (silica, 25% ethyl acetate in hexane). The reaction mixture was stirred overnight at room temperature, the layers were separated. The organic layer was dried over MgSO. and evaporated. Short path chromatography of the residual solid (silica, 5% ethyl acetate in hexane) afforded 3.8 g (71.0%) of the methylated product.

Workup

  1. customat room temperature
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over MgSO
  4. customand evaporated

Sources & evidence

ORD record
ord-0cc7dcd0f5f741d08ff84b26fe9c9715
Source dataset
uspto-grants-1992_01
Patent number
US05079260

Reaction notes

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