Butyl bromide → HCID 20462416, compound

Participants

Reaction Steps

Monosodium decane-1,10-diol is reacted with n-butyl bromide to give oily 10-n-butoxydecanol in a yield of 62% of theory. This is brominated with phosphorus tribromide in the presence of pyridine to give an oily product in a yield of 37% of theory. After reaction of this 10-n-butoxydecyl bromide with monosodium ethylene glycol, there is obtained oily 10-n-butoxydecyloxyethanol in a yield of 36% of theory, which is reacted with phosphorus tribromide in the presence of pyridine to give oily 10-n-butoxydecyloxyethyl bromide in a yield of 52% of theory. This is then reacted with methyl β-mercaptopropionate in the presence of sodium methylate to give a yield of 49% of theory of oily methyl β-(10-n-butoxydecyloxyethylthio)-propionate, reduction of which with lithium aluminium hydride gives a yield of 90% of theory of 3-(10-n-butoxydecyloxyethylthio]-propanol; m.p, 23°-27° C.

Provenance & Evidence