Octaethylene glycol Monobenzyl ether synthesis

9synthesis methods

Product Name:Octaethylene glycol Monobenzyl ether
CAS Number:477775-73-8
Molecular formula:C23H40O9
Molecular Weight:460.56

1611489-00-9 Synthesis

1611489-00-9
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477775-73-8
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Yield:477775-73-8 90%

Reaction Conditions:

with toluene-4-sulfonic acid in methanol at 20; for 36 h;Inert atmosphere;

Steps:

Synthesis of octa(ethylene glycol) monobenzyl ether (12)

A solution of 11(130.7 g, 0.2400 mmol) and TsOH (1 g) in 500 mL of anhydrous methanol wasplaced in a 1-L round bottom flask and stirred for 36h at room temperature. Afterremoval of solvent on rotavap, the oily product was dissolved in 1 L of dichloromethane,washed with saturated NaCl/NaOH solution (4 x 250 mL) and dried over anhydrous sodiumsulfate. Octa(ethylene glycol) monobenzyl ether (12) was obtained as a viscous reddish liquid by solvent evaporationand drying at 55 ^oC under vacuum for 12 h (111 g, 90.0%). ¹HNMR (500 MHz, CDCl₃) δ 7.27-7.38 (m, 5H), 4.59 (s, 2H), 3.60-3.77(m, 32H), 2.60 (t, 1H, J =5 Hz, -OH); ¹³C NMR (125 MHz, CDCl₃)δ 138.26, 128.29, 127.67, 127.51, 73.19, 72.46, 70.52-70.61 (br.), 70.33,69.42, 61.70.

References:

Zhang, Quanxuan;Ren, Hong;Baker, Gregory L. [Tetrahedron Letters,2014,vol. 55,# 22,p. 3384 - 3386] Location in patent:supporting information