Hydrochloric Acid → 2-(2-Methoxyethoxy)ethyl 4-hydroxybenzoate

Participants

Reaction Conditions

Reaction Steps

In a first step, an amount of 1 g (43 mmol) of sodium was dissolved in 25 of ml 2-(2-methoxyethoxy)ethanol. To the resulted solution an amount of 3 g (22 mmol) of methyl 4-hydroxybenzoate was added and the mixture was heated to 130° C. for 24 hours; after cooling to room temperature, it was acidified with a hydrochloric acid solution (3N) and extracted with ethyl acetate. The removal of the solvent under reduced pressure and column chromatography of the residue (silica gel, hexane:ethyl acetate 3:1) afforded 2-(2-methoxyethoxy)ethyl 4-hydroxybenzoate, in the form of a colourless oil in essentially quantitative yield.

Provenance & Evidence