Chloroacetic Acid → BnO-PEG5-CH2COOH

Participants

Reaction Conditions

Reaction Steps

Metal sodium (115 mg, 5.0 mmol) was added to pentaethylene glycol monobenzyl ether (328 mg, 1.0 mmol), and the mixture was stirred at 90° C. for three hours. Chloroacetic acid (47 mg, 0.5 mmol) was added to the mixture which was then stirred at 90° C. for 16 hours. Water was added to the mixture which was then washed with ethyl acetate. Next, the aqueous layer was made acidic by 1 N hydrochloric acid, followed by extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure to obtain 390 mg of crude [2-(2-{2-[2-(2-benzyloxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]acetic acid in the form of a reddish brown substance.

Provenance & Evidence