Methanol → Benzeneacetic acid, 3,4-dimethoxy-, methyl ester

HRID 987202Notes

Reaction equation

HRID 987202 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([OH:14])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].S(=O)(=O)(O)O.[CH3:20]O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([O:14][CH3:20])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 7139(3,4-Dimethoxyphenyl)acetic acid

Product 1

HCID 85213Benzeneacetic acid, 3,4-dimethoxy-, methyl ester

Procedure

3,4-Dimethoxyphenylacetic acid (80.0 grams, 0.41 mole), methanol (350 milliliters (mL)) and 2 mL of concentrated sulfuric acid were added to a reaction flask equipped with a Dean-Stark trap condensor and magnetic stirrer. The reaction mixture was maintained at reflux temperature overnight. After removal of unreacted methanol via a rotary evaporator, the product was dissolved in ether. The ether solution was washed twice in a sodium bicarbonate solution, washed twice with water and dried over anhydrous sodium sulfate. The ether was removed on a rotary evaporator, leaving 85 grams of methyl 3,4-dimethoxyphenylacetate as a viscous oil.

Workup

  1. customequipped with a Dean-Stark trap condensor and magnetic stirrer
  2. temperatureThe reaction mixture was maintained
  3. temperatureat reflux temperature overnight
  4. customAfter removal of unreacted methanol
  5. customvia a rotary evaporator
  6. dissolutionthe product was dissolved in ether
  7. washThe ether solution was washed twice in a sodium bicarbonate solution
  8. washwashed twice with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe ether was removed on a rotary evaporator

Sources & evidence

ORD record
ord-d819d8e41186402bbe0fb2fb93f983b1
Source dataset
uspto-grants-2003_10
Patent number
US06630597B1

Reaction notes

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