Benzene → HCID 67265372, compound

HRID 1685822Notes

Reaction equation

HRID 1685822 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[C:5]([O-:8])(=O)[CH3:6].[C:9]([O-])(=O)[CH3:10].[C:13]([O-])(=O)C.[Pb+4].[CH:18]1[CH:23]=[CH:22]C=[CH:20][CH:19]=1>CO>[CH3:13][O:8][C:5]1[CH:6]=[C:23]([CH3:22])[CH:18]=[CH:19][C:20]=1[CH2:2][C:1]([O:4][CH2:9][CH3:10])=[O:3]

Participants

4

Reactant 2

HCID 241BenzeneHCID 178418268HCID 178418268, compound

Product 1

HCID 67265372HCID 67265372, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of lead tetraacetate (16.8 g) in benzene (80 ml) was added a solution of 2-methoxy-4-methylacetophenone (5.35 g) in methanol (8.25 ml), and then boron trifluoride/diethyl ether complex (16.5 ml) was added dropwise to the mixture with stirring under ice cooling, and the mixture was stirred overnight at room temperature. The reaction mixture was quenched with cold water, and extracted with benzene, and the organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, water, and saturated brine, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1) to give ethyl 2-methoxy-4-methylphenylacetate (3.22 g).

Workup

  1. additionboron trifluoride/diethyl ether complex (16.5 ml) was added dropwise to the mixture
  2. stirringthe mixture was stirred overnight at room temperature
  3. customThe reaction mixture was quenched with cold water
  4. extractionextracted with benzene
  5. washthe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, water, and saturated brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-2cabd32dd2534579835513a94c4fd493
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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