Reaktion #1731763

Reaktionsgleichung

methyl 5-benzyloxy-2-hydroxybenzoate

cesium carbonate

methyl iodide

→

methyl 5-benzyloxy-2-methoxybenzoate

Ausbeute 90.2%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated
2. 2
   workup.DISSOLUTIONdissolved again in ethyl acetate
3. 3
   Waschenwashed with saturated brine
4. 4
   TrocknenThe organic layer was dried (over MgSO4)
5. 5
   Sonstigethe solvent was evaporated under reduced pressure
6. 6
   SonstigeThe residue was purified by column chromatography (Biotage cartridge 40+M, ethyl acetate:n-hexane=15:85→1:4)

Vorschrift

To a suspended solution of methyl 5-benzyloxy-2-hydroxybenzoate (3.91 g) and cesium carbonate (6.41 g) in acetone (100 ml) was added methyl iodide (1.41 ml), and the mixture was stirred at 50° C. for 6 hr. The reaction mixture was concentrated, dissolved again in ethyl acetate and washed with saturated brine. The organic layer was dried (over MgSO4), and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Biotage cartridge 40+M, ethyl acetate:n-hexane=15:85→1:4) to give methyl 5-benzyloxy-2-methoxybenzoate (3.72 g, 90%) as colorless crystals.

Quelle