Ethyl Acetate → HCID 57682892, compound

HRID 494996Notes

Reaction equation

HRID 494996 reaction equation
[CH2:1]([C:4]1[C:5]([O:16][CH2:17][O:18][CH3:19])=[C:6]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:7]([O:9]C)=[O:8])[CH:2]=[CH2:3].[OH-].[Na+].C(OCC)(=O)C.S([O-])(O)(=O)=O.[Na+]>CO>[CH2:1]([C:4]1[C:5]([O:16][CH2:17][O:18][CH3:19])=[C:6]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:7]([OH:9])=[O:8])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 516919Sodium BisulfateHCID 57682839HCID 57682839, compound

Product 1

HCID 57682892HCID 57682892, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.32 g of methyl 3-allyl-4-methoxy-2-(methoxymethoxy)benzoate was dissolved in 12 ml of methanol, and the obtained mixture was then stirred while cooling on ice. Thereafter, 2.97 ml of a 5 N sodium hydroxide aqueous solution was added to the reaction mixture, and the obtained mixture was then stirred at room temperature overnight. The reaction solution was cooled on ice, and ethyl acetate was added thereto. Then, the obtained mixture was adjusted to be approximately pH 5 with addition of a 5% sodium hydrogen sulfate aqueous solution. An organic layer was separated, and a water layer was extracted with ethyl acetate. The obtained organic layers were gathered. The combined organic layer was washed with water and a saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure, so as to obtain 1.19 g of the subject compound. This compound was used in the following reaction without further purification.

Workup

  1. temperaturewhile cooling on ice
  2. stirringthe obtained mixture was then stirred at room temperature overnight
  3. additionwas added
  4. customAn organic layer was separated
  5. extractiona water layer was extracted with ethyl acetate
  6. washThe combined organic layer was washed with water
  7. dry with materiala saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate
  8. customAfter removing the drying agent
  9. filtrationby filtration
  10. concentrationthe organic layer was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-d418ea26768e46daba302de5457c16e5
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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