Ethylene Oxide → Octadecyl sulfide

Participants

Reaction Steps

1-Octadecanethiol, 250 g. (0.87 mole), was dissolved in 250 ml of bis-(2-methoxyethyl) ether. Three grams (0.13 mole) of cut sodium spheres were added and the reaction mixture was transferred to a rocking autoclave and ~462 g. of ethylene oxide was bled into the autoclave over a period of 3 hours at 140°-160° C. The maximum pressure observed was 540 lbs. After all the ethylene oxide had been added, rocking was continued for an additional hour. The mixture was cooled, the bis-(2-methoxyethyl) ether was evaporated under reduced pressure, and the residue crystallized from hexane to give a white solid in 65% yield based on the octadecane thiol.

Provenance & Evidence