Hydrochloric Acid → Methyl methoxy-(4-methoxyphenyl)acetate

HRID 599615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 599615
C[O-].[Na+].[C:4](O)(=[O:6])C.C(O)(=O)C.IC1C=CC=CC=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:23][CH:22]=1.Cl>CO>[CH3:4][O:6][CH:27]([C:24]1[CH:23]=[CH:22][C:21]([O:20][CH3:19])=[CH:26][CH:25]=1)[C:28]([O:30][CH3:31])=[O:29]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 90266Methyl 4-methoxyphenylacetateHCID 10942334Sodium MethoxideHCID 12217721Iodo benzene diacetate

Produkt 1

HCID 10262525Methyl methoxy-(4-methoxyphenyl)acetateAusbeute 15,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A 28% solution of sodium methoxide in methanol (12.8 g) and iodobenzene diacetate (7.15 g) were added to a solution of methyl 4-methoxyphenylacetate (4.0 g) in methanol (60 mL), and the reaction solution was stirred at room temperature for five days. 1 N hydrochloric acid (67 ml) was added dropwise to the reaction solution under ice-cooling, and methanol was evaporated from the reaction solution under reduced pressure. Ethyl acetate was added to the remaining aqueous layer, and the organic layer was separated. The resulting organic layer was sequentially washed with a saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting solvent: heptane-ethyl acetate system) to obtain 725 mg of the title compound. The property values of the compound are as follows.

Aufarbeitung

  1. temperaturecooling
  2. custommethanol was evaporated from the reaction solution under reduced pressure
  3. additionEthyl acetate was added to the remaining aqueous layer
  4. customthe organic layer was separated
  5. washThe resulting organic layer was sequentially washed with a saturated sodium bicarbonate solution and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (eluting solvent: heptane-ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-e58ec8da09cd49e0aa1d169f65f5e68b
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897632B2

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