Methanol → Methyl 3,5-dimethoxyphenylacetate

HRID 11768

Reaction equation

HRID 11768 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([OH:14])=[O:13])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.S(=O)(=O)(O)O.[CH3:20]O>>[CH3:20][O:13][C:12](=[O:14])[CH2:11][C:5]1[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 138316(3,5-Dimethoxyphenyl)acetic acid

Product 1

HCID 592191Methyl 3,5-dimethoxyphenylacetate

Procedure

To a solution of 3,5-dimethoxyphenylacetic acid (1.99 g, 10.0 mmol) (Transworld) in methanol (20 mL) was added concentrated sulfuric acid (1.0 mL) and the reaction mixture was heated at reflux for 24 hours. The reaction mixture was concentrated in vacuo. The residue was then diluted with ethyl acetate (100 mL) and successively washed with water (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give the crude 3,5-dimethoxyphenylacetic acid methyl ester as a black oil which was used in the next step without further purification. (Yield 2.05 g, 97.6%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 24 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionThe residue was then diluted with ethyl acetate (100 mL)
  5. washsuccessively washed with water (50 mL) and brine (50 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-22aae1a312904b26991097295d0ce830
Source dataset
uspto-grants-2006_08
Patent number
US07098332B2

Linked notes

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