1-Dodecanethiol → Dodecylsulfanyl-3-(2,4,6-trichloro-phenyl)-prop-2-en-1-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(2,4,6-trichloro-phenyl)-prop-2-yn-1-ol (1.0 g; 4.2 mmol) in N-methyl-2-pyrrolidone (10 ml) and ethyl acetate (2 ml) at 2° C. was added sodium hydroxide (grind to powder) (0.19 g; 4.7 mmol). At 5° C. was added dropwise dodecanethiol (1.4 ml; 6.0 mmol). The reaction mixture was allowed to warm at 22° C. and was stirred for 30 min. The mixture was poured in water and ethyl acetate was added. Organic layer was washed three times with brine, dried over sodium sulfate and evaporated. The crude oil obtained was subject to flash chromatography (eluant: c-hexane/ethyl acetate 99:1 to 80:20) to afford 0.60 g (32% of theory) of dodecylsulfanyl-3-(2,4,6-trichloro-phenyl)-prop-2-en-1-ol as a yellow oil.

Provenance & Evidence