The general procedure for the synthesis of 3-hydroxyphenylacetylene from (3-hydroxyphenylalkynyl)trimethylsilane was as follows: (3-hydroxyphenylalkynyl)trimethylsilane was dissolved in a mixed solvent of THF (6 mL) and MeOH (6 mL), followed by the addition of 10% aqueous KOH solution (6 mL). The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the reaction mixture was neutralized with 1N HCl solution and the solvent was subsequently removed by rotary evaporation. The aqueous phase was extracted with CH2Cl2 and the organic phase was dried with anhydrous Na2SO4. Finally, purification by column chromatography (eluent: n-hexane/acetone, 5:1, v/v) afforded 3-hydroxyphenylacetylene (162.8 mg, 70% yield), the product was a yellow oil.
