Methyl iodide → Methyl 4-methoxyphenylacetate

HRID 48156

Reaktionsgleichung

Reaktionsgleichung von HRID 48156
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:15]I>O1CCCC1>[CH3:15][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Produkt 1

HCID 90266Methyl 4-methoxyphenylacetateAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

A solution of methyl 4-hydroxyphenylacetate (25.0 g, 0.147 mol) in tetrahydrofuran (50 ml) was added dropwise to a stirred suspension of sodium hydride (4.45 g of an 80% dispersion in oil, 0.147 mol) in tetrahydrofuran (150 ml) and the mixture was stirred for 90 minutes. A solution of methyl iodide (20.9 g, 0.47 mol) in tetrahydrofuran (50 ml) was added dropwise and the mixture was stirred overnight at room temperature. The solvent was removed in vacuo, and the residue was partitioned between water and ethyl acetate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was purified by chromatography on silica gel, eluting with ethyl acetate:hexane 1:9, to give methyl 4-methoxyphenylacetate (22.0 g) as a colourless oil.

Aufarbeitung

  1. stirringthe mixture was stirred overnight at room temperature
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between water and ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate was evaporated in vacuo
  9. customThe residue was purified by chromatography on silica gel
  10. washeluting with ethyl acetate:hexane 1:9

Quellen und Nachweise

ORD-Eintrag
ord-b18ace9b66fe460e9a61d18b4777618b
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703347B2

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