2-[2-(Benzyloxy)ethoxy]ethanol

Description

Benzyl-PEG3-alcohol is a PEG linker with an acid labile, benzyl protecting group and a reactive primary alcohol. The primary alcohol can react and further derivatize the compound. The hydrophilic PEG linker increases the water solubility of the compound in aqueous media.

Chemical Properties

Colorless to light yellow liquid

Uses

Di(ethylene glycol) benzyl ether may be used as an initiator in the preparation of linear-PLA (poly(L-lactide).

Synthesis

GENERAL METHOD: Dioxane (15 mL), benzyl chloride (25 mmol) and tetrabutylammonium bromide (0.4 g, 1.2 mmol) were sequentially added to a reaction flask, followed by addition of the mixture to a solution of diethylene glycol (75-125 mmol) containing KOH (1.6 g, 27.5 mmol). The reaction system was heated to 100-105 °C and the reaction was continuously stirred for 5-10 hours. Upon completion of the reaction, the reaction mixture was diluted with CHCl3 (15 mL) and water (10 mL). The organic layer was separated, washed with water (3 x 20 mL) and dried over anhydrous Na2SO4. The organic phase was concentrated under reduced pressure and the residue was purified by distillation through a Vigreux column to afford the target product 2-[2-(phenylmethoxy)ethoxy]ethanol. The specific reaction conditions, yields, physicochemical parameters and 1H NMR data are detailed in Table 6 of the literature.

IC 50

PEGs

References

[1] Synthetic Communications, 1986, vol. 16, # 1, p. 19 - 26
[2] Carbohydrate Research, 1986, vol. 150, p. 199 - 212
[3] Russian Chemical Bulletin, 2014, vol. 63, # 11, p. 2445 - 2454
[4] Izv. Akad. Nauk, Ser. Khim., 2014, # 11, p. 2445 - 2454
[5] Analytical Chemistry, 1992, vol. 64, # 15, p. 1685 - 1690