GB628497A - Improvements in or relating to the production of aryl-ª‰ú‘ª†-dihydroxypropyl ethers - Google Patents

Abstract

Aryl b : g -dihydroxypropyl ethers are prepared by treating a phenol with a substantially equimolecular amount of glycidol or b -methylglycidol at or above room temperature in the presence of a catalyst consisting of a quaternary ammonium salt or a tertiary amine which forms a salt in dilute hydrochloric acid. The reaction temperature should not exceed 95-100 DEG C. Specified tertiary amines are pyridine, quinoline, and dimethylaniline. Any phenol may be employed, e.g. homocyclic or heterocyclic, e.g. 8-hydroxy quinoline, and may be substituted or unsubstituted. The reaction may be carried out in a liquid medium, e.g. in an alcohol, glycol, glycol ether, aromatic hydrocarbon, aromatic hydrocarbon halogenated in the nucleus, or an aryl alkyl ether. The ether may be recovered in the usual manner. In the examples: (1) glycidol is treated with o-cresol in the presence of pyridine to give o-tolyl b : g -dihydroxypropyl ether; (2-7) glycidol is similarly treated with p-chlorophenol, a -naphthol, catechol, o-bromophenol, o-iodophenol, o-allyloxyphenol and p-methoxyphenol in the presence of pyridine or quinoline; (7-15) b -methylglycidol is treated with phenol, o-cresol, p-cresol, p-methoxyphenol, o-chlorophenol, p-chlorophenol and m-nitrophenol, using pyridine, quinoline, tri-n-propylamine or N-propylpiperidine as catalysts; (16) b -methylglycidol is treated with phenol in the presence of pyridine ethiodide to give b : g -dihydroxy-b -methylpropoxybenzene; (17-24) glycidol is treated with phenol, o-cresol, p-methoxyphenol, p-chlorophenol, and p-cresol, in the presence of pyridine ethiodide or methiodide or quinoline ethiodide as catalyst. Specification 470,181 is referred to.