Methanol → Methyl 2-(4-hydroxy-3,5-dimethoxyphenyl)acetate

HRID 1723996

Reaktionsgleichung

Reaktionsgleichung von HRID 1723996
[OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([CH2:10][C:11]([OH:13])=[O:12])=[CH:4][C:3]=1[O:14][CH3:15].[CH3:16]O.S(=O)(=O)(O)O>C(OCC)(=O)C>[CH3:16][O:12][C:11](=[O:13])[CH2:10][C:5]1[CH:4]=[C:3]([O:14][CH3:15])[C:2]([OH:1])=[C:7]([O:8][CH3:9])[CH:6]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 780934-Hydroxy-3,5-dimethoxyphenylacetic acid

Produkt 1

HCID 57436869Methyl 2-(4-hydroxy-3,5-dimethoxyphenyl)acetateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(4-Hydroxy-3,5-dimethoxy-phenyl)-acetic acid (9.5 g, 0.042 mmol) was added to methanol (260 mL) and sulfuric acid (8 mL). After completion of addition the reaction was heated at reflux overnight. The next day, the reaction mixture was cooled down and concentrated to yield a crude oil. The oil was re-dissolved in ethyl acetate, washed with water, brine, and dried over sodium sulfate, and filtered to be concentrated again. The crude material was purified using silica gel chromatography (50%:50% ethyl acetate:pentane) to yield the desired product (1.5 g, 75% yield based on recovered starting material).

Aufarbeitung

  1. additionAfter completion of addition the reaction
  2. temperaturewas heated
  3. temperatureat reflux overnight
  4. temperatureThe next day, the reaction mixture was cooled down
  5. concentrationconcentrated
  6. customto yield a crude oil
  7. washwashed with water, brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationto be concentrated again
  11. customThe crude material was purified

Quellen und Nachweise

ORD-Eintrag
ord-c6fa2b1f5a6e41bf913bb0b16b123be0
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07485283B2

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