Syntheses Of β-alkylthio Butanols, Butanethiols And Their Derivatives

In order to study the applicability of characteristic structural unit with a basic meat flavor proposed by Sun Baoguo, five series of flavoring compounds were synthesized by five different methods, which were 1-alkylthio-2-butanols, 1-alkylthio-2-butanones, alkyl 2-methoxy-butyl sulfides, 1-alkylthio-2-butanthiols and 4-alkylthio-4-methyl-2-pentanones.Seven 1-alkylthio-2-butanols were synthesized by 1,2-epoxybutane refluxing with various thiols for 2 hours under the action of sodium hydroxide in methanol, such as 1-ethylthio-2-butanol, 1-propylthio-2-butanol, 1-butylthio-2-butanol, 1-hexylthio-2-butanol, 1-octylthio-2-butanol, 1-furfurythio-2-butanol. Seven 1-alkylthio-2-butanones were synthesized by Swern oxidation of 1-alkylthio-2-butanols. The products were 1-ethylthio-2-butanone, 1-propylthio-2-butanone, 1-butylthio-2-butanone, 1-hexylthio-2-butanone, 1-octylthio-2-butanone, 1-furfurythio-2-butanone.Seven alkyl 2-methoxybutyl sulfides were obtained by refluxing 1-alkylthio-2-butanols with iodomethane for 3～4 hours under the action of sodium hydride in tetrahydrofuran. They were ethyl 2-methoxybutyl sulfide, propyl 2-methoxybutyl sulfide, butyl 2-methoxybutyl sulfide, hexyl 2-methoxybutyl sulfide, octyl 2-methoxybutyl sulfide and furfuryl 2-methoxybutyl sulfide.Six alkylthio-2-butanethiols were synthesized by 1,2-butylene sulfide refluxing with various thiols for 5～8 hours under the action of sodium hydroxide in methanol, such as 1-ethylthio-2-butanethiol, 1-propylthio-2-butanethiol, 1-butylthio-2-butanethiol, 1-hexylthio-2-butanethiol, 1-octylthio-2-butanethiol, 1-furfurythio-2-butanethiol.Five 4-alkylthio-4-methyl-2-pentanones were synthesized by refluxing 4-methyl-3-pentene-2-one with various thiols for 20 hours in tetrahydrofuran, with piperidine as catalyst. They were 4-ethylthio-4-methyl-2-pentanones,...