Octyl phenyl ether → Octyl phenyl ether

Participants

Reaction Steps

A sample of (4-octyloxyphenyl)phenyl iodonium toluenesulfonate (in short C8-O-iodonium) was prepared according to the method of Crivello et al (J. Polym. Sci: Part A: Polymer Chemistry, (1989), 27, 3951-3968) by reacting hydroxytosyloxyiodobenzene with octyloxybenzene in a mixture of acetonitrile and acetic acid. Octyloxybenzene was previously obtained by reacting sodium phenate with bromooctane in a water/toluene mixture by phase transfer catalysis in the presence of tetrabutyl ammonium bromide. To 8 g of this compound in solution in 60 ml of methylethylketone (MEK) are added 3.02 of potassium bis-fluorosulfonylimide. The mixture is stirred magnetically for 1 hour at room temperature and filtrated to remove the insoluble potassium toluenesulfonate. The solution is poured into a flask which is adjusted to be adapted on a rotary evaporator and the solvent is evaporated. The last traces of MEK are eliminated under a vacuum primary pump and the residue is in the form of a viscous oil (8.04 g, 98%). There is added thereto an equal weight of dichloromethane enabling to give a fluid mixture which can be handled. Solubility tests are made in adjusted flasks after adding a given quantity of mixture and evaporation of the volatile fraction (CH2Cl2). Results of the tests are given below:

Provenance & Evidence