Hydrogen Peroxide → Methyl 2-(2-isobutoxyphenyl)acetate

HRID 2249624Notes

Reaction equation

HRID 2249624 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH:13]=[O:14])[CH:2]([CH3:4])[CH3:3].P([O-])(O)(O)=O.[Na+].OO.Cl([O-])=O.[Na+].[C:27](=O)([O-])[O-:28].[K+].[K+].IC>C(#N)C.O.C(OCC)(=O)C.CN(C)C=O>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]([O:28][CH3:27])=[O:14])[CH:2]([CH3:4])[CH3:3]

Participants

11

Reactant 6

HCID 784Hydrogen PeroxideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178165132-(2-Isobutoxyphenyl)ethanalHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 17816558Methyl 2-(2-isobutoxyphenyl)acetateYield 52.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent4×HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 17 g of 2-(2-isobutoxyphenyl)ethanal in 170 ml of acetonitrile, 29 g of sodium dihydrogenphosphate dissolved in 200 ml of water and subsequently 15 g of 30% aqueous hydrogen peroxide are added, and further 16 g of sodium chlorite dissolved in 80 ml of water is dropwise added, and the mixture thus obtained is stirred at ambient temperature for one hour. Ethyl acetate and water added to the reaction mixture, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue thus obtained is mixed with 22 g of potassium carbonate and 200 ml of N,N-dimethylformamide. While cooling the mixture with ice water, 19 g of iodomethane is added, and the mixture thus obtained is stirred at ambient temperature for 30 minutes. Ethyl acetate and water are added to the reaction mixture, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=10:1) to obtain 10.4 g of methyl 2-(2-isobutoxyphenyl)acetate as a colorless oily product.

Workup

  1. additionis dropwise added
  2. customthe mixture thus obtained
  3. customthe organic layer is separated
  4. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent is distilled off under reduced pressure
  7. customThe residue thus obtained
  8. additionis added
  9. customthe mixture thus obtained
  10. stirringis stirred at ambient temperature for 30 minutes
  11. customthe organic layer is separated
  12. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  13. dry with materialdried over anhydrous magnesium sulfate
  14. distillationthe solvent is distilled off under reduced pressure
  15. customThe residue thus obtained
  16. customis purified by silica gel column chromatography (eluent; hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-b784eca3c76e41539023dd3f76bce4a7
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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