Prepn. of chloracetoxyalkyl acrylates or methacrylates - from hydroxyalkyl acrylates, chloracetyl chloride, tert. amines, polar solvents

摘要

Prepn. of (I) chloroacetoxyalkyl-acrylate and methacrylate is by reaction of (II) a hydroxyalkyl (meth)acrylate with (III) chloracetylchloride in the presence of a tert. amine, washing the prod. obtd. with water and opt. distilling. (II) is reacted with (III) in the mol. ratio 1:1.05-1.3 in the presence of an equimolar amt. of tert. amide to (II), in benzene, toluene, xylene (or a mixt.) as solvents Chloracetoxyalkyl (meth)acrylates are produced in a high yield. There is no excess amine hydrochloride present to reduce the yield on water washing the reaction mixt. or to cause polymerisation on distillation of the end prods. In an example to 1 mol. of 2-hydroxyethyl-methacrylate cooled to 0 degree C, is added simultaneously over 120 minutes 1.1 mol. of chloracetyl chloride in 280 ml toluene and 1 mol. of tri-n-butyl amide in 100 ml toluene. After the reaction has been completed at room temp. the solvent phase is washed, neutralised and removed to give a 79.7% yield of chloracetoxyethyl methacrylate.