Effects of solvents and molecular weights of polyethylene glycols on the allylation of phenoxide

Abstract

In the present study, the synthesis of allyl phenyl ether by reacting sodium phenoxide and allyl bromide using PEGs as phase transfer catalysts either in a homogeneous phase or in a two-phase reaction was studied. The reaction in a homogeneous phase was carried out using EtOH as the solvent and the reaction in a two-phase was carried out using aprotic solvents, such as dichloromethane, chlorobenzene, ethyl ether, cyclohexane and n-decane. In the homogeneous phase reaction, the effects of the molecular weights of PEGs on the initial reaction rate were investigated in detail. The aprotic properties of the PEGs were used to explain the variation in experimental results due to the use of different molecular weight PEGs. The reactivity of the reaction, which was influenced by the organic solvents in a two-phase reaction, was also examined. The effects of the polarity of the solvents, the solubility of sodium phenoxide in the organic phase and the viscosity of the solution on the two-phase reaction were employed to explain the experimental results satisfactorily. m