Hydrochloric Acid → Deca-2,8-diyne-1,10-diol

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2.12 g of commercially available 1,7 octadiyne (20.0 mmol) was first combined with 80 mL of Et2O and 30 mL of THF. The solution was cooled to -78° C. and treated with 15.6 mL (42 mmol, 2.7M) of BuLi. After 0.5 hr at this temperature, 4.8 g of paraformaldehyde (160 mmol) was added and stirred for a further 2.0 hr at 0° C. At 10% soln. of aqueous HCl was added and the crude product extracted into diethyl ether. Treatment of the ether extracts with sat. NaHCO3 and brine, followed by solvent removal and column chromatography (60:40 EtOAc: Hexane) gave pure deca-2,8-diyne-1,10-diol in 50% yield.

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