تفاعل #1483140

معادلة التفاعل

Phenol

potassium carbonate

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

→

title compound

المردود 52.9%

(2-(2-methoxyethoxy)ethoxy)benzene

المردود 52.9%

المذيبات

DMSO

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe solution heated to 90° C. for 18 h
2. 2
   درجة الحرارةcooled to r.t
3. 3
   غسيلwashed with 1M potassium hydroxide (3×300 mL)
4. 4
   تجفيفdried (Na2SO4)
5. 5
   تركيزconcentrated in vacuo

الإجراء التجريبي

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).

المصدر