Yield:-

Reaction Conditions:

Stage #1: decaethylene glycol;benzyl bromidewith sodium hydride in tetrahydrofuran at 20; for 16 h;
Stage #2: with water;ammonium chloride in tetrahydrofuran;

Steps:

4-48.A

Step A; Decaethylene glycol monobenzyl ether; [Show Image] Sodium hydride (35 mg, 0.872 mmol) and benzyl bromide (52 μl, 0.436 mmol) were added to 5 mL of a solution of commericially available decaethylene glycol (200 mg, 0.436 mmol) in THF, and the mixture was stirred at room temperature for 16 hours. Aqueous saturated ammonium chloride was added to the mixture, followed by extraction with ethyl acetate. The extract was washed with saturated saline and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 168mg of crude decaethylene glycol monobenzyl ether as a colorless oil.

References:

EP1854792,2007,A1 Location in patent:Page/Page column 207-208