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

HRID 1106868Notes

Reaction equation

HRID 1106868 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 (3 g, 0.0153 mol) was dissolved in methanol (50 ml) and, thereafter, conc. sulfuric acid (0.05 ml) was added to the resulting solution, followed by heating at the reflux temperature for 2 h. Thereafter, the solvent was evaporated and the residue was neutralized with an aqueous solution of sodium bicarbonate, followed by extraction with ethyl acetate. The organic extract was dried with sodium sulfate, followed by evaporation of the solvent and drying under vacuum to yield the oil compound methyl 3,4-dimethoxyphenylacetate (3.2 g) as a colorless oil.

Workup

  1. temperatureby heating at the reflux temperature for 2 h
  2. customThereafter, the solvent was evaporated
  3. extractionfollowed by extraction with ethyl acetate
  4. extractionThe organic extract
  5. dry with materialwas dried with sodium sulfate
  6. customfollowed by evaporation of the solvent
  7. customdrying under vacuum

Sources & evidence

ORD record
ord-6262a11d7968460bb75fa2276746e4c1
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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