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According to the method of J. Cole et al., J. Chem. Soc., 244 (1962), a mixture of toluylacetylene (200 mmol), 2-(4-bromophenyl)-1,3-dioxalane (200 mmol), dimethylformamide (500 ml), and copper iodide (I) (300 mmol) was heated while stirring for 5 hours. After allowed to cool, 500 ml of 6M hydrochloric acid was added and stirred for 1 hour. It was extracted with 500 ml of toluene, and the organic layer was washed with water thrice and dried with anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by a silica gel column chromatography (eluent:toluene) to obtain 120 mmol of 4-(2-(4-methylphenyl)ethynyl)benzaldehyde.

1. temperaturewas heated
2. temperatureto cool
3. stirringstirred for 1 hour
4. extractionIt was extracted with 500 ml of toluene
5. washthe organic layer was washed with water thrice
6. dry with materialdried with anhydrous magnesium sulfate
7. distillationThe solvent was distilled off
8. customthe residue was purified by a silica gel column chromatography (eluent:toluene)