3-Ethynyltoluene

40230-90-8

766-82-5

The general procedure for the synthesis of 3-methylphenylacetylene from 3-tolyl(trimethylsilyl)acetylene was as follows: 3-[(trimethylsilyl)ethynyl]toluene (1 mmol), an inorganic base (potassium tert-butanol, sodium tert-butanol, potassium hydroxide, sodium hydroxide, or potassium trimethylsilylated, sodium trimethylsilylated, 0.05 mmol) were added in turn to a 10 mL sealed tube, as well as 2 mL of DMA or DMSO as solvent. The mixture was heated and stirred in an oil bath at 60 °C for 7 h. The reaction progress was monitored by TLC. Upon completion of the reaction, equal amounts of homotrimethylbenzene or n-undecane were added as internal standards for quantitative analysis of the crude product. The exact yields of the products were determined by GC and GC-MS. The yields of the products were 74%, 73%, 74%, 80%, 93%, and 90% when DMSO was used as the solvent and potassium tert-butanol, sodium tert-butanol, potassium hydroxide, sodium hydroxide, or potassium trimethylmethylsilylated, sodium trimethylmethylsilylated were used as the catalysts, respectively. And when DMA was used as the solvent, the yields of the products were 61%, 60%, 63%, 73%, 82%, and 83%, respectively, using the same catalysts.