Synthesis of [14C]-labelled glycidyl and glycerol ethers of aliphatic and aromatic alcohols

Abstract

The synthesis of [14C]-labelled glycidyl ethers and the corresponding glycerol ethers is described for the monofunctional compounds 1-dodecanol and ortho-cresol and the bifunctional compounds 4,4′-dihydroxy-3,3′,5,5′-tetramethyl biphenyl and 1,6-hexanediol. The synthesis is based on reaction between the alcohol and [U-14C]-epi-chlorohydrin (1). The aromatic compounds have been converted to the corresponding glycidyl ethers by using sodium hydroxide and the aliphatic compounds by using tin(IV) chloride as a catalyst. Thus radio-labelled glycidyl ethers were obtained in yields between 50–80%, with a chemical purity of >92% and a radiochemical purity of >95% by HPLC. The specific activities of the glycidyl ethers were approximately 0·2 mCi/mmol for the monofunctional compounds and approximately 0·4 mCi/mmol for the bifunctional compounds. Copyright © 2000 John Wiley & Sons, Ltd.