Synthesis
General procedure for the synthesis of 4-tert-butylphenylacetylene from the compound (CAS:135883-30-6): the raw material (5.0 g, 21.7 mmol) was dissolved in a solvent mixture of 50 mL of methanol and 50 mL of dichloromethane, and finely powdered potassium carbonate (6.0 g, 43.5 mmol) was added. The suspension was stirred at room temperature for 3 hours. After completion of the reaction, the mixture was filtered through a bed of diatomaceous earth, water was added to the filtrate and extracted with ether. The ether layers were combined and washed twice with water (50 mL each), then the extract was dried with anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure to give a colorless liquid product. The structure of the product was confirmed by 1H-NMR spectroscopy (CDCl3, 300 MHz): δ 1.33 (s, 9H), 3.04 (s, 1H), 7.35 (d, 2H, J = 8.3 Hz), 7.45 (d, 2H, J = 9.0 Hz). Mass spectrometry (EI) showed a molecular ion peak m/z 158.0 [M]+. The separation yield was 96% (3.3 g).
References
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[2] Tetrahedron Letters, 2011, vol. 52, # 51, p. 6942 - 6947
[3] Organic Letters, 2014, vol. 16, # 3, p. 948 - 951
[4] Tetrahedron, 1997, vol. 53, # 45, p. 15515 - 15534
[5] Russian Journal of Organic Chemistry, 2000, vol. 36, # 8, p. 1157 - 1162
