2,4,6-Tris(2',4',6'-trimethylphenylethynyl)mesitylene
Chemistry Department, Southwest Missouri State University, 901 South National Avenue, Springfield, MO 65804, USA
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Molecules 2000, 5(4), M147; https://doi.org/10.3390/M147
Submission received: 24 February 2000
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Accepted: 28 February 2000
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Published: 28 April 2000
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
The experimental procedure follows the general synthesis of arylalkynes reported by Sonogashira [1]. Thus a solution of 2,4,6-triiodomesitylene (1.14 g, 2.29 mmol), 2-ethynylmesitylene (1.1 g, 7.638 mmol), bis(triphenylphosphine)palladium dichloride (0.089 g), copper iodide (0.041 g) and triphenylphosphine (0.225 g) in triethyl amine (40 mL) was refluxed under an argon atmosphere for 48 h [2,3]. The solvent was removed in vacuo and the solid residue washed with dichloromethane and water. The residue was dissolved in hot toluene and allowed to crystallize slowly yielding 0.95 g of the title compound as fine pale green needles (76 % yield).
M.p. 318-322 °C.
IR (KBr): 3019, 2960, 2920, 2848, 2197, 1618, 1485 cm-1.
1H NMR (200 MHz, CDCl3): 2.31 (9H, s, CH3), 2.53 (18H, s, CH3), 2.83 (9H, s, CH3), 6.94 (6H, s, Ar-H).
Anal. Calcd. for C42H42, C: 92.25, H: 7.74. Found C: 91.60, H: 7.75.
Supplementary Materials
Acknowledgements
The authors gratefully acknowledge financial support from Southwest Missouri State University.
References and Notes
- Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627.
- 2-Ethynylmesitylene was prepared according to the general procedure in reference 1.
- Full characterization of 2-ethynylmesitylene is reported in: Tinnenmans, A. H. A.; Laarhoven, W. H. Tetrahedron 1979, 35, 1537.
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Jeffries, L.; Bosch, E. 2,4,6-Tris(2',4',6'-trimethylphenylethynyl)mesitylene. Molecules 2000, 5, M147. https://doi.org/10.3390/M147
AMA Style
Jeffries L, Bosch E. 2,4,6-Tris(2',4',6'-trimethylphenylethynyl)mesitylene. Molecules. 2000; 5(4):M147. https://doi.org/10.3390/M147
Chicago/Turabian StyleJeffries, Laura, and Eric Bosch. 2000. "2,4,6-Tris(2',4',6'-trimethylphenylethynyl)mesitylene" Molecules 5, no. 4: M147. https://doi.org/10.3390/M147
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