1,4-Butanediol → HCID 14435001, compound

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:

1. customThe 1,4-butanediol dipropiolate was prepared
2. temperatureheated
3. temperatureto reflux under nitrogen until 6.44 g
4. customof water was azeotroped over into a Dean-Stark trap
5. washThe reaction mixture was washed with 10% sodium carbonate aqueous solution until the pH value of the mixture
6. washwashed with deionized water several times
7. dry with materialdried over sodium carbonate
8. customThe solvent was removed on a Rotavapor

ORD record

ord-c1784af174d049a0a64be8848ecd011f

Source dataset

uspto-grants-1996_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05559189