1,4-Butanediol → HCID 14435001, compound

Participants

Reaction Steps

The 1,4-butanediol dipropiolate was prepared as follows. A solution of 27.5 g. (0.393 mole) of propiolic acid in 75 ml of benzene was reacted with 16.07 g. (0.179 mole) of 1,4-butanediol in the presence of 1.5 g. paratoluenesulfonic acid as a catalyst. The reaction mixture was stirred and heated to reflux under nitrogen until 6.44 g. of water was azeotroped over into a Dean-Stark trap. The reaction mixture was washed with 10% sodium carbonate aqueous solution until the pH value of the mixture was basic, then washed with deionized water several times and dried over sodium carbonate. The solvent was removed on a Rotavapor and 1,4-butanediol dipropiolate was obtained in 90% yield as white crystals with a melting point of 59° C. The structure of 1,4-butanediol dipropiolate is as follows:

Provenance & Evidence