Reaktion #1909464

Reaktionsgleichung

orcinol

potassium carbonate

benzyl bromide

→

title compound

Ausbeute 57.0%

3-Benzyloxy-5-methyl-phenol

Ausbeute 57.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction is filtered
2. 2
   workup.ADDITIONThe mixture is then diluted with Et2O
3. 3
   Extraktionextracted with water
4. 4
   TrocknenThe organic layer is dried (Na2SO4)
5. 5
   Sonstigethe solvent is removed in vacuo
6. 6
   Sonstigeto afford crude product that
7. 7
   Sonstigeis absorbed on silica gel
8. 8
   Sonstigepurified by flash chromatography

Vorschrift

A 0° C. mixture of orcinol (10.0 g, 80.6 mmol) and 325 mesh potassium carbonate (12.25 g, 88.6 mmol) in DMF (100 mL) is treated dropwise with benzyl bromide (6.91 g, 40.4 mmol). The mixture was then warmed to rt and stirred for 20 hours under N2. The reaction is filtered, and the filtrate is acidified with 1 N HCl. The mixture is then diluted with Et2O and extracted with water. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 5/1 hexanes/ethyl acetate to afford 4.88 g (57%) of the title compound. Rf=0.40 (2/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calculated for C14H14O2 214, found 215 (M+1, 100%).

Quelle