Methanol → Methyl 3-hydroxy-4-methoxyphenylacetate

HRID 506154Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 506154
[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

Komponenten

4

Edukt 3

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

Produkt 1

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

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d7f17909a3214625a3a2465d1557403b
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781591B2

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