Benzyl 2-ethylhexyl sulfoxide

The molecule of the title compound, C15H24OS, shows S conformations for the S atom and the asymmetric C atom of the isooctyl group. The long axes of the molecules are directed along the c axis. In the crystal structure, the molecules are linked by weak intermolecular bifurcated C—H⋯O hydrogen bonds.

The molecule of the title compound, C 15 H 24 OS, shows S conformations for the S atom and the asymmetric C atom of the isooctyl group. The long axes of the molecules are directed along the c axis. In the crystal structure, the molecules are linked by weak intermolecular bifurcated C-HÁ Á ÁO hydrogen bonds.

Comment
Sulfoxides have been widely used in the separation of palladium from other platinum-group metals(PGMs) by solvent extraction (Xu et al., 2006). The experimental results indicated that the title compound exhibited excellent extraction property to PGMs (Xu et al.,2007). A similar disulfoxide ligand 1,6-bis(benzylsulfinyl)hexane and its Copper(II) and Cadmium(II) dimeric complexes were obtained (Li et al.,2003).
The stucture of the title compound, (I), Fig.1, exhibit the S conformation for the sulfur atom and asymmetric carbon atom of the isooctyl group. The long axes of the molecules are directed along the c axis. Additionally, the crystal structure exhibits weak intermolecular bifurcated C-H···O hydrogen bonds (for geometric details see Table 1).

Experimental
The title compound was prepared refering to the literature method (Li et al.,2003;Iitaka et al., 1986) with little modification.
Sodium hydroxide (99%, 0.273 g, 0.0068 mol) and 1-isooctyl mercaptan (1.000 g, 0.0068 mol) were dissolved in anhydrous ethanol (50 ml) at 70°C, and then benzylchloride (0.86 g, 0.0068 mol) was added to the above solution with stirring over 1 h. The solution was extracted with CH 2 Cl 2 after addition 400 ml of water. Benzyl isooctyl sulfide(1.412 g, 0.0060 mol) was obtained after evaporation of CH 2 Cl 2 . Yield: 87%. Hydrogen peroxide (30%, 0.0043 mol) was added dropwise to a solution of benzyl isooctyl sulfide (1.000 g, 0.0042 mol) in acetic acid (60 ml) on ice bath with a vigorously stir for 1 h. 500 ml of water was added. The solution was extracted with CH 2 Cl 2 , and the product of benzyl isooctyl sulfoxide(0.943 g, 0.0037 mol) was obtained after evaporation of CH 2 Cl 2 . Yield: 88%. It was characterized by recording its infrared and NMR spectra. White single crystals of the title compound were obtained by slow evaporation of its mixed solution including n-hexane and dichloromethane.

Refinement
All H atoms were placed in calculated positions and subsequently constrained to ride on their parent atoms, with C-H distances of 0.93 Å (C-aromatic) and 0.97 Å (C-methyl). The U iso (H) values were set at 1.2 U eq (C aromatic) and 1.5 U eq (C methyl).   as those based on F, and R-factors based on ALL data will be even larger.