Hydrochloric Acid → 3-(Octadecylsulfanyl)propanoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 86.8 gm (0.25 mole) octadecyl bromide, 29.2 gm (0.275 mole) 3-mercaptopropionic acid and 90.0 gm isopropanol at 80° C. was added 95.0 gm (0.275 mole) 40% aqueous potassium carbonate solution dropwise. The mixture was heated at 80° C. for 8 hours and then cooled to 60° C. After adding 125.0 gm water and 36.8 gm of 30% hydrochloric acid solution, the mixture was slowly heated to 94° C. while distilling aqueous isopropyl alcohol from the reaction. The product separated as an oil from the aqueous phase. It was isolated using a separatory funnel and washed with hot water. Upon cooling, the product solidified as a light tan waxy solid. It was dried in a vacuum oven at 50° C. to yield 91.35 gm (98%)

Provenance & Evidence