Synthesis of acyclic quaternary ammonium compounds containing ω-alkoxyethyl and 2-hydroxyethyl substituents at the nitrogen atom

A series of acyclic symmetric quaternary ammonium chlorides Me 2 (HOCH 2 CH 2 )N + (CH 2 CH 2 O) n R Cl – ( n = 1, R = n -C 9 H 19 ; n = 2, R = n -C 6 H 13 ; n = 3, R = n -C 3 H 7 ) was synthesized by alkylation of the corresponding tertiary amines Me 2 N(CH 2 CH 2 O) n R with ethylene chlorohydrin in a two-phase system, using water as a solvent. The tertiary amines were synthesized in a heterogeneous system organic phase—aqueous phase, using an aqueous solution of Me 2 NH and a solid alkali. The intermediate monoethers of ethylene, diand triethylene glycol were obtained in high yield via a phase-transfer alkylation in dioxane, using solid KOH. The proton and carbon atom signals in the NMR spectra of the synthesized amines and ammonium chlorides were assigned based on the data of heteronuclear correlations ( 1 H, 13 C).