Methanol → Methyl 3-hydroxy-4-methoxyphenylacetate

HRID 506154Notes

Reaction equation

HRID 506154 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].OS(O)(=O)=O.[CH3:19]O>>[CH3:19][O:12][C:11](=[O:13])[CH2:10][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([OH:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1605623-Hydroxy-4-methoxybenzeneacetic acid

Product 1

HCID 10465267Methyl 3-hydroxy-4-methoxyphenylacetateYield 90%

Procedure

To a stirred solution of 3-hydroxy-4-methoxyphenyl acetic acid (24.8 g, 136 mmol) in 200 mL of MeOH was added 1 mL of H2SO4 and the reaction mixture was heated at reflux overnight. The methanol was removed by evaporation in vacuo and the residue was poured into saturated NaHCO3 solution and extracted with EtOAc (3×150 mL). Combined organic extracts were then washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to yield 23.9 g (90% yield) of 3-hydroxy-4-methoxyphenyl acetic acid methyl ester as a yellow oil.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux overnight
  3. customThe methanol was removed by evaporation in vacuo
  4. additionthe residue was poured into saturated NaHCO3 solution
  5. extractionextracted with EtOAc (3×150 mL)
  6. washCombined organic extracts were then washed with brine
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d7f17909a3214625a3a2465d1557403b
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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