Reactions with Betaines, XXIII. Reactions of Nitrogen- and Sulphur-Betaines with Reactive Halides

Article abstract of DOI:10.1007/BF00810092

Trimethylammonium acetic betain (1) reacts with phenacyl bromide and ethyl bromoacetate, respectively, to give the ester bromides 2 and 7.These can be hydrolyzed with aqueous sodium hydrogencarbonate at 20 deg C to yield besides 1 both C-benzoyl-methanol (3) and the glycolic acid ester 8, respectively.The reaction can also be performed in one step by reacting the betain (1) (with can act as a base) in a double molar ratio with the active halide. - Keywords: Trimethylammonium acetic acid betain; Trimethylammonium acetic acid phenacyl ester bromide; Trimethylammonium acetic acid acetoxy ethyl ester bromide; Phenacyl alcohol; Ethyl glycolate