The protocol, 3-methyldec-1-yn-3-ol (1a) was chosen to perform the dimerization process. The optimal conditions for synthesis of 8,13-dimethylicosa-9,11-diyne-8,13 (2a) with high efficiency when using copper-catalyzed, N,N,N′N′-tetramethylethylenediamine as a ligand and CCl4 and methanol solvents in atmospheric pressure were determined. The structure of the obtained compound was proved by IR, 1H-NMR and 13C-NMR spectroscopy.

The title compound, C16H22O2, was synthesized in order to obtain its guest-free form because `wheel-and-axle'-shaped molecules tend to crystallize from solutions as solvates or host–guest molecules. It crystallizes in the monoclinic space group P2/c with two crystallographically non-equivalent molecules, one situated on an inversion center and the other on a twofold axis. The rod-like 1,3-diyne fragments have the usual linear geometry. In the crystal, O—H ... O bonds form eight-membered rings of the R 4 4(8) type, linking molecules into layers. The Hirshfeld surface analysis indicates that the largest contributions are from intermolecular H...H (ca 71%) and H...C/C...H (ca 19%) contacts. The energies of the frontier molecular orbitals were determined by DFT calculations at the B3LYP/def2-TZVP level of theory.