Reaktion #1483140

Reaktionsgleichung

Phenol

potassium carbonate

1-bromo-2-(2-methoxyethoxy)ethane

→

title compound

Ausbeute 52.9%

(2-(2-methoxyethoxy)ethoxy)benzene

Ausbeute 52.9%

Lösungsmittel

DMSO

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe solution heated to 90° C. for 18 h
2. 2
   Temperaturcooled to r.t
3. 3
   Waschenwashed with 1M potassium hydroxide (3×300 mL)
4. 4
   Trocknendried (Na2SO4)
5. 5
   Einengenconcentrated in vacuo

Vorschrift

Phenol (15.0 g, 0.159 mol), potassium carbonate (26.4 g, 0.191 mol, 1.2 eq) and tetramethylethylenediamine (0.92 g, 7.95 mmol, 0.05 eq) were dissolved in DMSO (100 mL) and stirred at r.t. for 30 minutes. Then 1-bromo-2-(2-methoxyethoxy)ethane (30.56 g, 0.166 mol, 1.04 eq) was added, the solution heated to 90° C. for 18 h and cooled to r.t. The reaction mixture was diluted with ethyl acetate (600 mL), washed with 1M potassium hydroxide (3×300 mL), dried (Na2SO4) and concentrated in vacuo to afford the title compound (16.50 g, 52%) as an orange oil. 1H NMR (500 MHz, (CD3)2CO) δ: 7.27 (dt, J=8.5 Hz, 1 Hz, 2H), 6.94 (dd, J=8 Hz, 1 Hz, 2H), 6.92 (dt, J=8 Hz, 1 Hz, 1H), 4.12 (t, J=5 Hz, 2H), 3.80 (t, J=5 Hz, 2H), 3.64 (t, J=5 Hz, 2H), 3.50 (t, J=5 Hz, 2H), 3.29 (s, 3H).

Quelle