Reaktion #2065142

Reaktionsgleichung

Water

Orcinol monohydrate

NaH

Benzyl bromide

→

title compound

Ausbeute 48.5%

3-Benzyloxy-5-methylphenol

Ausbeute 48.5%

Lösungsmittel

N,N-dimethylformamide

N,N-dimethylformamide

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred at room temperature for 2 hours
2. 2
   ExtraktionThe reaction mixture was extracted 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
   SonstigeAfter the solvent was evaporated
6. 6
   Sonstigethe residue was purified by flash column chromatography (silica gel, 3:1 hexane:ethyl acetate)

Vorschrift

Orcinol monohydrate (7.10 g, 50 mmol) in N,N-dimethylformamide (20 mL) was added dropwise to a mixture of NaH (95%, 24 g, 100 mmol) in N,N-dimethylformamide (60 mL) and the mixture was stirred at room temperature for 20 min. Benzyl bromide (8.55 g, 50 mmol) in N,N-dimethylformamide (20 mL) was added dropwise to the mixture and stirred at room temperature for 2 hours. Water (100 mL) was added slowly to the reaction mixture. The reaction mixture was extracted with ethyl acetate (3×100 mL) and then the organic phase was washed with brine (2×50 mL) and dried over Na2SO4. After the solvent was evaporated, the residue was purified by flash column chromatography (silica gel, 3:1 hexane:ethyl acetate) to give the title compound as a yellow oil (5.20 g, 48%). 1H-NMR (300 MHz, CDCl3) δ7.39 (m, 5H), 6.40 (s, 1H), 6.29 (t, J=5.3 Hz, 1H), ), 6.26 (s, 1H), 5.25 (s, 1H), 4.99 (s, 2H), 2.26 (s, 3H).

Quelle