Water → HCID 23470789, compound

Participants

Reaction Steps

A mixture of 16.7 g (0.1 mole) of p-mercaptoacetanilide, 4 g of sodium hydroxide, 40 ml of water, 40 ml of 1,2-dimethoxyethane, and 0.39 g (0.11 mole) of 3-chloropropanol is heated in a steam bath with stirring for 30 minutes. Two liquid phases are formed, and TLC indicates that the reaction is substantially complete. The mixture is distilled in vacuo to remove 1,2-dimethoxyethane, and the oily mixture which separates is triturated with cold water until it solidifies. The crude product is recrystallized from ethanol to obtain a by-product: the disulfide derived from the starting mercapto compound. The ethanol filtrate is concentrated, and the residue is triturated with ether-hexane to obtain 15.7 g of the desired product. Recrystallization from ethyl acetate-hexane gives 11.8 g of 3-(p-acetamidophenylthio)propanol which shows the correct IR and NMR spectra.

Provenance & Evidence