Uses
2,4-Hexadiyne-1,6-diol may be used as a starting material in the synthesis of thiarubrine A (an antibiotic). It may also be used to synthesize disodium salt of 2,4-hexadiyne 1,6-disulfate (HDDS).
General Description
2,4-Hexadiyne-1,6-diol can be prepared from propargyl alcohol. 2,4-Hexadiyne-1,6-diol readily undergoes polymerization when heated under vacuum or inert gas atmosphere.
Synthesis
The reaction substrate acetylenic alcohol 0.112 g (2.0 mmol), triethylamine 0.202 g (2.0 mmol), and CuAl-LDH catalyst 0.29 g were weighed and placed together in a glass flask, and 10 mL of the organic solvent toluene was added, and the reaction was stirred for 16 hr at room temperature and pressure. After stopping the reaction, the reaction mixture solution in the flask was filtered. The filtered solid was washed with toluene for 2-3 times, then dried at 40-150 C for 2-20 h and used directly in the next catalytic cycle. The filtrate was combined with the washed solvent and concentrated by rotary evaporator, then separated over a silica gel column with hexane/ethyl acetate as eluent to give 2,4-diyne-1,6-hexanediol in 86% yield.
