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

HRID 1587723Notes

Reaction equation

HRID 1587723 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>>[CH3:20][O:13][C:12](=[O:14])[CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1

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 (20 g) and concentrated sulphuric acid (1 ml) in methanol (70 ml) were stirred at reflux for 16 hours. Methanol was removed by evaporation and the residue poured into cold water (250 ml) with stirring). Extraction into ethyl acetate (2×100 ml), washing with saturated NaHCO3 (100 ml) and brine (100 ml) followed by evaporation under reduced pressure gave, as an orange oil, 3,4-dimethoxyphenylacetic acid methyl ester (18 g); NMR (DMSO-d6) 3.57(s,2H); 3.62(s,3H); 3.73(s,6H); 6.75(dd,1H); 6.88(s,1H); 6.89(d,1H).

Workup

  1. temperatureat reflux for 16 hours
  2. customMethanol was removed by evaporation
  3. additionthe residue poured into cold water (250 ml)
  4. extractionExtraction into ethyl acetate (2×100 ml)
  5. washwashing with saturated NaHCO3 (100 ml) and brine (100 ml)
  6. customfollowed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-db62163df37042c38e810b0dab475933
Source dataset
uspto-grants-1993_06
Patent number
US05219848

Reaction notes

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