Unsaturated bis-tertiary glycols and processes for their production

摘要

The invention comprises unsaturated bistertiary glycols of the general formula: wherein R represents a hydrogen atom or the methyl group, X represents a halogen atom or the trifluoromethyl group, Y represents a hydrogen atom or a halogen atom and each Z represents hydrogen or, together, they represent an additional bond; and their preparation by (I) reacting a 2-phenyl acetoin of formula: with at least 1 molar excess of an organometallic compound of formula: wherein M is the group Hal-Mg-, where Hal is a halogen atom, or when the two symbols z together represent an additional bond M may also be lithium, sodium or potassium, and then hydrolysing the reaction product obtained, and (z) optionally hydrogenating in the presence of a hydrogenation catalyst an acetylene of formula I to an ethylene. Metal acetylides III may be formed directly in liquid ammonia or during reaction from the alkyne and a suspended alkali metal hydroxide. Organic magnesium halides III may be prepared in tetrahydrofuran, for example reacting ethyl magnesium bromide with acetylene. 2-Phenyl-acetoins II may be prepared from phenyl magnesium bromides reacted with diacetyl or from acetophenones reacted with acetylides to give a product to which water is added.