Reaktion #1833637

ord-f2dd04c40d0c4f64abcaee6e0e4d1750

Reaktionsgleichung

O
water
COC(=O)c1cc(OCc2ccccc2)ccc1O
methyl 5-(benzyloxy)-2-hydroxybenzoate
O=C([O-])[O-].[K+].[K+]
K2CO3
CI
iodomethane
COC(=O)c1cc(OCc2ccccc2)ccc1OC
methyl 5-(benzyloxy)-2-methoxybenzoate
Ausbeute 98.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationfiltered
  2. 2
    Sonstigecollected the solid
  3. 3
    workup.DISSOLUTIONThe solid was dissolved in EtOAc (300 mL)
  4. 4
    Waschenwashed with water (50 mL) and brine (100 mL)
  5. 5
    Trocknendried over Na2SO4
  6. 6
    Filtrationfiltered
  7. 7
    Einengenconcentrated under reduced pressure

Vorschrift

To a mixture of methyl 5-(benzyloxy)-2-hydroxybenzoate (10.6 g, 41.1 mmol) and K2CO3 (11.3 g, 82.2 mmol) in DMF (100 mL) was added iodomethane (2.60 mL, 49.3 mmol) drop wise over 5 minutes. The resulting mixture was stirred at room temperature overnight. The reaction mixture was poured into water (400 mL), filtered, and collected the solid. The solid was dissolved in EtOAc (300 mL), washed with water (50 mL) and brine (100 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to give methyl 5-(benzyloxy)-2-methoxybenzoate (10.4 g, 98%) as a yellow solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09150526B2uspto-grants-2015_10