GB828395A - A process for the manufacture of tetrahydrofurfuryl-ammonium compounds - Google Patents

Abstract

Tetrahydrofurfuryl-ammonium compounds of the general formula <FORM:0828395/IV (b)/1> (wherein R1, R2 and R3 each represent an alkyl group containing up to three carbon atoms and A is an anion) are made by cyclizing a compound of the general formula <FORM:0828395/IV (b)/2> (wherein X is a free or esterified hydroxy group, e.g. a halogen atom or an alkanoyloxy group) by treating same with a dehydrating agent, and, when X is an esterified hydroxy group, transforming this into a free hydroxy group by hydrolysis or, in the case of a halogen atom, by reaction with a silver salt of an alkanoic acid and hydrolysis of the alkanoyloxy group thereby introduced. Suitable dehydrating agents are dehydrating acids (such as oxalic, phosphoric, succinic, sulphuric or p-toluene-sulphonic acid), acidic salts (such as monosodium phosphate or potassium pyrosulphate) or calcinated salts (such as copper sulphate or zinc chloride). (2,5 - Dihydroxy - 4 - alkanoyloxy - hexyl) - trialkyl-ammonium chlorides are made by reacting a 2,5 - dihydroxy - 4 - alkanoyloxy - hexyl chloride with an appropriate trialkyl amine. Trialkyl - (2,5 - dihydroxy - 4 - halogeno - hexyl)-ammonium salts are made by reacting an a - alkanoyl - d - halogeno - g - valerolactone with the appropriate trialkylamine, reacting the product with sulphuryl chloride, hydrolysing and decarboxylating the reaction product and reducing the carbonyl group in the compound so obtained with sodium boron hydride. Trialkyl - (2,4,5 - trihydroxy - hexyl) - ammonium salts are made by treating the appropriate trialkyl - (2 - hydroxy - 4 - halogeno - 5 - oxo - hexyl) - ammonium salts with an alkaline-earthmetal carbonate to give the corresponding 4-hydroxy compounds and catalytically reducing the oxo group in these compounds to a hydroxy group. Trialkyl - (2,5 - dihydroxy - 4 - acetoxy - hexyl)-ammonium salts are made from the appropriate trialkyl - (2,5 - dihydroxy - 4 - chloro - hexyl)-ammonium salts by reacting same with silver acetate.