Reaktion #569268

Reaktionsgleichung

Water

Orcinol monohydrate

NaH

Benzyl bromide

→

title compound

Ausbeute 31.0%

3-Benzyloxy-5-methylphenol

Ausbeute 31.0%

Lösungsmittel

DMF

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 2 h
2. 2
   Extraktionfollowed by extraction with ethyl acetate (3×100 mL)
3. 3
   WaschenThe organic phase was washed with brine (2×50 mL)
4. 4
   Trocknendried over Na2SO4
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe residue was then purified by flash column chromatography (3:1 hexane:ethyl acetate)

Vorschrift

Orcinol monohydrate (7.10 g, 50 mmol) in DMF (20 mL) was added dropwise to NaH (95%, 2.4 g, 100 mmol) in DMF (60 mL). The reaction mixture was stirred at room temperature for 20 min. Benzyl bromide (8.55 g, 50 mmol) in DMF (20 mL was then added dropwise and the reaction mixture was stirred at room temperature for 2 h. Water (100 mL) was added slowly followed by extraction with ethyl acetate (3×100 mL). The organic phase was washed with brine (2×50 mL), dried over Na2SO4, and concentrated in vacuo. The residue was then purified by flash column chromatography (3:1 hexane:ethyl acetate) to give the title compound as a yellow oil (3.15 g, 31%). 1H-NMR (300 MHz, CDCl3) 2.26 (s, 3H), 4.99 (s, 2H), 5.25 (s, 1H), 6.26 (s, 1H), 6.29 (t, 1H), 6.40 (s, 1H), 7.39 (m, 5H).

Quelle