Condensation of Industrial Alcohols with Arylalkenes and Biological Activity of the Resulting Ethers

The corresponding alkyl aryl ethers were obtained in yields exceeding 50% by catalytic condensation of aromatic olefins—styrene and α-methylstyrene—with alcohols (butanol and 2-ethylhexanol), as well as with ethylene glycol monoethers (ethyl cellosolve and butyl cellosolve), in the presence of various cation exchangers: 1-n-butoxy-1-phenylethane, 1- (2-butoxypropan-2-yl) benzene, 1- (2-ethylhexyl) oxyethylbenzene, 1-methyl-1- (2-methylhexyl) oxyethylbenzene, 1- (2-ethoxyethoxy) ethylbenzene, 1- (2-ethoxyethoxy) -1-methylethylbenzene, and 1- (2-butoxyethoxy) ethylbenzene. Conditions enabling preparative isolation of the target compounds in high yields were determined. Among the cation exchangers tested, the highest yields of ethers were achieved using the BENJION DVC-8 UPS cation-exchange resin; in the presence of the TOKEM-102 cation exchanger, the yields of the target compounds were slightly lower. The structures of the obtained compounds were confirmed by 1H and 13C NMR spectroscopy, as well as by mass spectrometry. Using the 1H NMR spectrum of 1-n-butoxy-1-phenylethane recorded in CDCl3 as an example, signals characteristic of the C3H7 group protons were observed in the high-field region at δH 0. 96 ppm and in the ranges 1. 33–1. 43 ppm and 1. 55–1. 61 ppm, while the proton of the methine group bound to the oxygen atom appears as a doublet at δH 1. 50 ppm (J = 5. 7). For 1- (2-ethoxyethoxy) -1-methylethylbenzene and 1- (2-butoxyethoxy) ethylbenzene, the mass spectra show the presence of M – CH3+ cations formed via elimination of a methyl group from the molecular cation radical, with the intensity of the M – CH3+ signal not exceeding 30%. Aryl alkyl ethers are also characterized by the presence of the C6H5+ cation, which can form as a result of elimination of a CH3• radical from the cation with m = 91. The antiaggregation and anticoagulation activities of the synthesized substances were evaluated, and butyl and isooctyl ethers of styrene and α-methylstyrene exhibited antiaggregation and anticoagulation properties somewhat lower than those of the reference standards acetylsalicylic acid and sodium heparin.