Ethyl Acetate → Methyl 5-acetyl-2,4-dimethoxybenzoate

HRID 2293552Notes

Reaction equation

HRID 2293552 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].F[C:16](F)(F)[C:17](OC(=O)C(F)(F)F)=[O:18].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(O)(=O)C>[C:17]([C:10]1[C:11]([O:13][CH3:14])=[CH:12][C:3]([O:2][CH3:1])=[C:4]([CH:9]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:18])[CH3:16]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9845Trifluoroacetic anhydrideHCID 137451Benzoic acid, 2,4-dimethoxy-, methyl esterHCID 516892Sodium Bicarbonate

Product 1

HCID 21477069Methyl 5-acetyl-2,4-dimethoxybenzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 1.00 g portion of methyl 2,4-dimethoxybenzoate was suspended in 0.58 ml of acetic acid, and 1.44 ml of dry trifluoroacetic acid anhydride was added under ice-cooling, followed by stirring at room temperature for 12 hours. Under ice-cooling, a saturated sodium bicarbonate aqueous solution and ethyl acetate were added, and then insoluble matter was removed by celite filtration. The thus obtained filtrate was extracted with ethyl acetate, washed with water and saturated brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1-80:1) to give 0.99 g of methyl 5-acetyl-2,4-dimethoxybenzoate.

Workup

  1. temperaturecooling
  2. temperatureUnder ice-cooling
  3. custominsoluble matter was removed by celite filtration
  4. extractionThe thus obtained filtrate was extracted with ethyl acetate
  5. washwashed with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under a reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1-80:1)

Sources & evidence

ORD record
ord-f7013f0047334928a99a9eba37790f0e
Source dataset
uspto-grants-1997_11
Patent number
US05686482

Reaction notes

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