Benzene → 2-Benzyloxyethyl propiolate

Participants

Reaction Steps

A mixture of 2 g of 2-benzyloxyethanol, 2.8 g of propiolic acid, 0.005 g of p-toluenesulfonic acid and 25 ml of benzene was refluxed with stirring for six hours while water formed was removed by a Dean-Stark water separator. After the reaction was completed, the reaction solution was washed successively with a 5% aqueous sodium bicarbonate solution and a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the obtained residue was subjected to silicagel column chromatography to yield 2.39 g of 2-benzyloxyethyl propiolate (compound 16).

Provenance & Evidence