反应 #1483140

反应方程式

Phenol

potassium carbonate

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

→

title compound

收率 52.9%

(2-(2-methoxyethoxy)ethoxy)benzene

收率 52.9%

溶剂

DMSO

ethyl acetate

反应条件

后处理

1. 1
   温度the solution heated to 90° C. for 18 h
2. 2
   温度cooled to r.t
3. 3
   洗涤washed with 1M potassium hydroxide (3×300 mL)
4. 4
   干燥dried (Na2SO4)
5. 5
   浓缩concentrated in vacuo

实验过程

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).

来源