Synthesis of Bis(aryloxyethyl) Vinyl Ethers via Phase-Transfer-Catalyzed Nucleophilic Displacement on 2-Chloroethyl Vinyl Ether

Article abstract of DOI:10.1021/jo00151a013

Bis(aryloxyethyl) vinyl ethers can be prepared in high yield by using sodium hydroxide, bis(phenols), and 2-chloroethyl vinyl ether (CEVE) with a tetraalkylammonium salt phase-transfer catalyst.The displacement reaction of the bis(phenol) dianion proceeds in high yield only if both excess CEVE and base are employed.Nucleophilic displacement is considerably faster than elimination reactions involving solvent or catalyst.Small amounts of water have little effect on the reaction.The synthesis has been extended to the preparation of related monoaryloxyethyl vinyl ethers.